ATD: All Things Divorce

Navigating Modern Love in a Digital World with Ilana Dunn

Merel Family Law

Ever wondered why dating feels simultaneously easier and harder than ever before? In this illuminating conversation, dating expert Ilana Dunn pulls back the curtain on modern relationships with refreshing candor and practical wisdom.

Ilana shares her fascinating journey from heartbroken music industry professional to Hinge's social media maven to creator of the wildly popular "Seeing Other People" podcast. Her story reminds us that sometimes our greatest setbacks—like being laid off during a pandemic—can become our greatest opportunities when we follow our authentic passion.

The digital dating landscape has completely transformed how we connect, but Ilana explains why having more options doesn't necessarily lead to more meaningful relationships. She offers invaluable insights on navigating dating apps effectively, identifying genuine compatibility beyond texting chemistry, and recognizing the most important green and red flags (spoiler: it's about how you feel, not superficial traits).

For those in relationships, Ilana shares the communication strategies that prevent small frustrations from becoming relationship-ending resentments. Her creative approach to maintaining excitement through intentional traditions like "date card days" demonstrates how simple thoughtfulness can keep long-term love thriving.

Perhaps most powerfully, Ilana provides compassionate guidance for those healing after breakups. Her advice on giving yourself permission to grieve, leaning on your support network strategically, and recognizing when you're truly ready to date again offers a roadmap through one of life's most challenging transitions.

Whether you're newly single after divorce, perpetually swiping without success, or seeking to strengthen an existing relationship, this episode delivers practical tools for finding and maintaining authentic connection in our complex digital world.

Jonathan Merel:

Welcome to ATD, the All Things Divorce Podcast. I'm your host, Jonathan Merel. Welcome to the All Things Divorce Podcast. I'm Jonathan Merel, your host Today. I'm really, really excited about our episode because you know we're usually here. We're talking about splitting up divorce, the laws of divorce, how sad it is, how things can be depressing, and dealing with children, and all that unfun stuff. Today, we're going to talk about some more fun stuff, at least most of it. We have on with us today the one and only Ilana Dunn. She's the host of Seeing Other People podcast, which is a huge podcast. If you don't know about it, you're probably living under a rock. She's basically a celebrity. She's on our podcast today. We are delighted to have her here. Welcome, Ilana.

Ilana Dunn:

Thank you so much. I always, whenever I hear an intro about myself, I'm like, wow, that person sounds awesome, Good for them, and like it just still to this day doesn't feel like it could be me, but I appreciate the kind words. It's you.

Jonathan Merel:

It is you. I mean, this girl has more Instagram following than anyone I've ever seen Maybe Kardashian, but she's second. I mean, she's close and if she's not at Kardashian level, she's getting there. Anyways, I'm pumped to have you here. I'm excited about what we're going to talk about. We're going to talk about dating. We're going to talk about relationships. We're going to talk about things that you know.

Jonathan Merel:

As a divorce lawyer, I don't necessarily ever get to talk about this fun stuff. Whenever a client comes in, sure, you hear about their story, but it's usually unfortunately it didn't work out. We're talking about the beginning of relationships which could turn into marriages, which, unfortunately, could turn into divorces, but we're not worried about that today. We're talking about how does the relationship starts, what goes on in the dating world today, and we have the best expert we could possibly have, so let's get into it. First of all, let everybody know who is Ilana Dunn, how did you get to become the utmost authority in dating, and tell us where you came from and who you are and what we're dealing with today.

Ilana Dunn:

It all started the day I was born. I came out of the womb and said I'm going to be a dating coach and I'm going to help people on dating apps, which don't exist. Yet I fell into this. I actually, in my early twenties I was really pursuing a career in the music industry. I was so passionate about it I never in a million years would have imagined that I would want to leave. But after a few bad dating and relationship experiences with guys who also worked in the industry whether on the label side, the management side or musicians themselves I got to the point where I couldn't even listen to music anymore. It made me too sad and it was this huge it was. It was.

Ilana Dunn:

It was very depressing and it was this huge wake up call of like this industry, this atmosphere, does not work for me anymore.

Ilana Dunn:

I need to get out as far away as possible and I spent months and months looking for jobs and at the time I was dating I was using all the apps. I actually had only found success, and by success I mean I would go on a lot of dates, but all of my dates actually came from Hinge, despite being on all of the apps, and suddenly Hinge was hiring for somebody to run their socials and to really be the face of their app on social media, and I was essentially using all the same skills that I was applying to music, but I'd just be applying to dating instead. And so I had this light bulb moment of wow. If I could use, like all of the heartbreak and pain I feel, and the skills I have to help one single person out there not end up feeling as depressed and heartbroken as I do right now, it'll all be worth it. And I got the job and hit the ground running from there.

Jonathan Merel:

So this is all based around the career change. Basically that got you involved with Hinge. So this, like you literally were fully enthrusted into, like the dating scene because you worked for the dating scene yes, that's crazy. That's crazy. So things started in Hinge. Where are you? Where are you based out of New York? I think you said yes.

Ilana Dunn:

I'm in New York city, and dating in New York city while working for one of the most up and coming dating apps was a really fun and interesting experience, and it was when I joined Hinge. I was like the 34th employee at the time and so it was very much startup mode Throw shit at the wall and see what sticks and so it was a creative playground. I was having the best time. I started, you know, opening up over time about what was going on in my dating life, not necessarily like, oh, this asshole said this thing to me on a date screw him.

Ilana Dunn:

But, like this happened, and this is how I feel and this is really hard. And the more I opened up about it, the more it resonated and the more messages I was getting from people thanking me for sharing how hard it was. And from there I said I want to start a podcast because, yeah, these 60 second videos are helpful, but how much more helpful could we be if we talk about different dating topics at length? And I started a podcast for Hinge called Dating Sucks in 2020. We recorded the first episode the first week of March in 2020. Good times. Recorded the rest of it from my parents' basement and really found my purpose. Found what I love to do, Got laid off November 2020, and I immediately knew I was not going to apply to work anywhere else. I did not want to go run social at another company. I found what I love to do and I was going to make it work on my own.

Jonathan Merel:

Well, I mean being in New York. I feel like New York is just the epicenter of the dating world. I mean, obviously you've got LA, you've got Chicago, you've got other cities, but I mean there's just you know, whether it be the show, friends or Sex in the City. I mean, and just knowing people I mean I have so many friends in New York I mean I don't think there's a better place to go after college than living as a single person. After college You're in New York City, you got your job and there's just a million people in the dating pool that are in similar situations. So I mean, how did being in New York kind of you know direct this whole career Because this isn't necessarily something that you could experience everywhere else being in New York is such a crucial part of it, I think.

Ilana Dunn:

I actually think being in New York as a single person is both a pro and a con, because, to your point, there are a million people, there are so many single people out there, there are so many people you could date. So then, when you're trying really, really hard and it's not working, it's so easy to say, like, well, what's wrong with me? There are all these people out there. I can't find my person, other people clearly can. I see it all over my Instagram feed. Everyone's in relationships, getting engaged, getting married. It must be a me problem. So I definitely faced a lot of that too, and I think that's actually what made me so relatable and what made me really good at my job was I understood how hard it was. I mean, I have friends who went on one date from an app and now that's the person they're married to and like, that's just that's, that's the exception, you know. And so, yes, there are so many positives that come from being in a city this big with so many people to meet, but it also can make it hard.

Jonathan Merel:

Yeah, exactly. So obviously you know your career's going like this. You've got ups and downs. You've got Hinge, you've got Pod. How did it get to the podcast? Seeing other people Like, obviously you had the first podcast that was related to Hinge. That didn't kind of go the way you wanted to COVID hits, whatever. Now you know you kind of are blank slate. What happens? What happens after that?

Ilana Dunn:

So I took about six weeks off between the day I lost my job and the day I started seeing other people. That was a really rough six weeks for me. Losing this job was like losing a part of my identity. I would get recognized on the street not as oh, it's Ilana Dunn, but as oh, it's Ilana from Hinge. That was my Instagram handle, that was who I was, and so it felt like a breakup. Losing this job. It felt like a breakup of a relationship that maybe I actually should have done sooner, but I didn't feel I didn't have the strength to do it, and so I spent those six weeks like coloring my feelings in adult curse word coloring books but, also knowing like, okay, this is a good thing, like I felt a weight off my shoulders.

Ilana Dunn:

I felt like I suddenly have all the creative control in the world again and I can make this whatever I want it to be. And the great thing was because I had this kind of built in audience from my time at Hinge because I had the podcast before people were waiting for it to come back. I was getting so many messages of when is the podcast coming? What are you going to do next? We want more content, and so when I launched Seeing Other People the first week of January 2021, there were all these people waiting for it and so excited and suddenly I didn't have to play by someone else's rule book.

Ilana Dunn:

I mentioned that when I started at Hinge, it was very startup mode. By the time I ended, it had been acquired by Match Group. There were suddenly so many people above me that needed to approve everything I was doing, and every single thing needed to fit into different goals, and so it was very scripted and curated versus now I could speak freely, I could talk about whatever I wanted. I didn't have to have anyone approve it. It was just what I thought it should be, and so I think that opened up a whole new world of guests.

Ilana Dunn:

I could have topics I could talk about, things I could share, and it really just kind of took off. I mean, I told myself I'm going to give myself six months to make it work and people think like, oh, I started seeing other people and it, just like that, became my job. I freelanced for the first year and a half. I was producing other people's podcasts, I was running other people's social media accounts, and seeing other people was just one piece of the puzzle. Over time it became a bigger piece and a bigger piece and I grew on social and that became a huge part of my career too. And I never really checked in at a six month mark, I just kept going.

Jonathan Merel:

So I mean, I guess you could say, the losing your job at Hinge was the biggest blessing, in disguise looking, back.

Ilana Dunn:

Best thing that ever happened to me Right.

Jonathan Merel:

I mean that just opened the door. I mean I think a lot of people have that moment, I think, in their career, where they catch a bad break and it sounds like it's the end of the world. But like, I feel like people can either, you know, be sorry, feel sorry for themselves and, you know, be miserable, or you could do something about it. And you did something about it and here you are and if you didn't have that thing happen, you know you might've been still under the thumb of hinge and all the red tape and not being able to do what you wanted.

Ilana Dunn:

Yeah, and, to be honest, I was miserable my last six months of working there, like I was crying every day. I was going to HR with all these problems about all these people. I was not in a good place, and so it really was the best thing that ever could have happened to me, because I felt stuck. I felt like, well, I found this thing I love to do. I suddenly my confidence went from a hundred to zero, because I'm being told no every five seconds by these people that I really, really dislike.

Ilana Dunn:

And so you know how am I going to go pitch myself to? You know, in my mind I'm like there's two other places I could go and do this at. That'd be Betches or Barstool. But I have no confidence to pitch myself and say you should want me. And so, you know, when I got, I was, it was in a Zoom call. I'm losing my job and I'm texting my friends. I just lost my job. I'm starting a podcast, like it really was everything I needed to happen, and I think you could relate it to divorce or breakups, where someone feels stuck for so long. But it's comfortable, it feels safe, it feels like, well, this is liberating.

Ilana Dunn:

Yeah, and so when it ends even if it's not necessarily what you wanted or maybe it's what you wanted in the back of your mind, but you were never going to do it yourself and it took the other person doing it it sets you free.

Jonathan Merel:

Well, that's a lot of it. Is that people, you know, for kind of making one analogy to divorce, like you said, people are comfortable and they don't necessarily know what's on the other side. They know they're probably not so happy, but you know, I'll keep the status quo, I'm fine with how things are. And then when there is that moment where things do change whether it be the other spouse making the move or you know the just the come to Jesus moment, like I got to do something about this. I can't live like this anymore when they do realize what's on the other side, it's like I said, it's liberating, it's a new chapter, it's like rejuvenating, it's a new life. And like rejuvenating, it's a new life and I mean, look, that's dating, that's marriage, that can be a lot of things. Once you kind of get out of the rut that you're in, you have more perspective and how shitty it was before and how great it is now. So yeah, that's definitely a parallel.

Jonathan Merel:

All right, so we start the podcast. Tell us about the podcast. Like, did you, is it the same now that you thought it would be at the beginning? Has it kind of morphed into something different? Tell us how you got to where you are with the podcast today.

Ilana Dunn:

It has evolved so much. From the start, it started as one episode a week with some type of expert guest, whether that was a therapist, an author, someone who specializes in attachment styles. It was always either an expert guest or somebody with a big audience. So a comedian, an influencer, someone who was on a show. It was always like someone like that. Over time, I realized like, yeah, those episodes are good. However, those people aren't, you know, out in the field, really in it.

Ilana Dunn:

And so I started to get listeners reaching out, wanting to come on and talk about, you know, their breakup or getting an abortion or getting an STD and having to navigate that and having to navigate that. And I was like, you know what? How freaking powerful would it be to actually have these conversations? Because no one else mainstream is doing it. But this is what people are actually experiencing. And so I launched a new episode each week on Thursdays called Unfiltered, and my listeners, my friends, anyone comes on anonymously to share what they've really been through and how it's impacted them and it you know I love dating.

Ilana Dunn:

People always ask like, am I sick of talking about dating? Like I'm married now? How do I still talk about dating? Every single aspect of your life impacts the way you show up in your dating life and your relationships. And your dating life and your relationships impact how you show up in your dating life and your relationships. And your dating life and your relationships impact how you show up in every single other aspect of your life. So you know I've had people come on to talk about getting cancer and how that impacted their relationships or losing a family member or, or you know, a partner, and how that impacted the way they date.

Ilana Dunn:

I have had people talk about every single topic under the sun and it keeps it so like genuinely real. Yeah, and I mean I still do both of those episodes every week. I do some solo episodes and actually this week I started a new series on Mondays with my husband called Co-Hosts for Life, where we're talking about our marriage, our lives, what's actually going on.

Ilana Dunn:

So it's definitely evolved as I've grown up too, but I think the coolest part about it is it launched January of 2021. I had my first date with Jake, my now husband, in February of 2021.

Jonathan Merel:

Oh my God. So it's like the whole process. Did you talk about dating him throughout the podcast?

Ilana Dunn:

I did and eventually, you know, he came on and I introduced him to people and then we talked about moving in together and then getting engaged. And so there are a handful of listeners who have been there from the beginning and it is so cool that they've really seen this all unfold. And I used to worry will being in a relationship make me less relatable to my listeners? And, if anything, they've all expressed that it gives them hope of like if Ilana can turn things around and go from her dumpster fire of a dating life to finding this person she feels so secure and comfortable with, so can I?

Jonathan Merel:

That's great. I mean you keep it real. That's really what people want. I mean, no one wants to listen to a podcast full of like bullshit or like fairy tales, like people want to be in the trenches. They want to hear about the good stuff, but all the shitty stuff that happens to people, I mean, and even the ugly stuff, stds like I'm sure there's like abuse that people confront obviously all the time, which we obviously get a lot of just you know terrible people, that people you know good people run into. I mean these are the realities.

Ilana Dunn:

I've also had countless episodes of people coming to talk about dating after divorce. So for your listeners definitely recommend checking those out.

Jonathan Merel:

I mean dating after divorce is a huge topic. I mean I keep in touch with clients even after just to kind of check in and see how they're doing, and that's a big part of it too. I mean we have an in-house divorce coach at our firm which kind of helps people deal with like the emotional toll and just kind of the change in people's lives obviously from going to being in a marriage to getting out and dating and then after the divorce, like getting the support to just get out there and experience like the new part of their life. Some people are like rah, rah, I can't wait, let's go. I'm going out four nights a week, every night, let's go. And some people are like I can't even bring myself to like get out there.

Jonathan Merel:

So I mean there's definitely extremes, you know, during divorce, after divorce, and obviously you know dating in general. So yeah, I want to get into like talking, getting your advice about dating. Yes, is dating today harder than ever? What is your thought on it? I mean, obviously you've got a million apps and things and technology that was never available before. Does this stuff make it harder? Does it make it easier? What's your take on that?

Ilana Dunn:

You know, looking at it from a thousand foot view, you would think it makes it easier. It seems like there's more ways to meet people than ever before, but there's also more ways to meet people than ever before. But there's also more ways to meet people than ever before.

Ilana Dunn:

And nobody's really taught us how to use them properly. And so, yeah, you can be on 50 dating apps, but if you're not actually crafting a profile that represents you and shares your personality and shows off you know what it would be like dating you, then no one's going to swipe right on you. You could be on 50 dating apps, but if you're not intentionally swiping on people you would actually have something in common with or be excited to meet, you're not going to end up going on dates that lead to a second date. It seems like there's a million ways to meet people, but it's so hard. I mean, everyone I talk to, all of my listeners, want to meet people in real life and I'm like OK, are you going to singles events? No, that's scary.

Jonathan Merel:

Right. Well, isn't that part of the problem with the apps? It's like you get so used to it. I mean, I have my kids, you know they're teenagers in high school and I'm like do you guys even know how to talk to people? Every time it's like a Snapchat or it's a DM or it's a you know you're texting. There's no human interaction. I mean, do apps take away an entire generation's ability to actually talk face to face? And like, how does that impact people when you finally do meet someone off the app?

Ilana Dunn:

It's hard. We've been trained for almost like a decade now to swipe speak and so, yeah, even if you do, you know, match with somebody, have an amazing texting conversation, feel like there's a great vibe chances are, when you meet in person, that's not going to translate to a real connection. There are so many people who are amazing texters who in real life, their texting vibe doesn't match their actual personality, and so what I see happen all the time is people get their hopes up and get so excited about somebody. They start picturing their future with someone before they've even met them in person. Sometimes they could even be talking to them for weeks, if not months, before meeting, and then you meet them in person, you're like, oh, this is really awkward, there's nothing here, and you feel stupid because you've wasted so much time, but you still want to see it through because you've already invested that time, so it's really really hard to spend.

Ilana Dunn:

Also, you could spend so much time on an app. Let's say you spend an hour on an app swiping right on people. Maybe you swipe right on 50 people. Maybe 20 of those people match with you. Maybe you start conversations with 10 of them, because you know starting conversation just because you match doesn't mean you're going to actually send the first message. You might be waiting for 10 of them, but you start conversations with 10 of them. Five of them respond, three of them. It turns into a conversation, one of them turns into a date, and that's the problem.

Jonathan Merel:

Is there a progression of okay, you match, you start texting. Does do something like not even get to like a phone call for sure?

Ilana Dunn:

like you say, phone call anyone under the age of 30 is not anyone. But, like 90 of people are terrified to do that. They don't want to write a phone. They They'd rather text text text text. Text me versus having a phone call or a FaceTime could save you so much wasted time and energy. That's my point. That's what I'm saying.

Jonathan Merel:

Like. It's like you said. There are people who could be amazing texters or who knows. They're probably using fucking AI to respond and act normal when they're really creepy, or not like normal at all and like just picking up the phone, hearing the tone in someone's voice, hearing like natural reactions or compliments, or even like a laugh. Yep Can give you so much information that you're not getting just by reading some texts. It's crazy to me that people will go straight from a text to a date and they have no clue like what the person sounds, like, how they interact. That's crazy to me. But then you're telling me that you think that's the norm. A lot of people don't even talk on the phone.

Ilana Dunn:

Yeah, there are. There are a handful of people who do want to do that. But then they'll say like hey, like let's, do you want to talk on the phone? Oh, it's easier to like share the story, or I'd like to do a phone call before meeting. And then people are like ew, and I think that's crazy. But here's the thing for the people who are willing to do it someone who's not willing to do it, that's not going to be their person anyway.

Jonathan Merel:

Right, right. And then obviously you know you hear about all right people have just said apps they just want to hook up. It's a one night stand thing. Like, how do people get through that? I mean, I don't know if it's more prevalent with guys being the stereotypical people who you know just want a one and done, but I'm sure it happens both ways. I guess you know how do you, how do you flesh that out? I'm sure there are more apps that are more kind of directed towards that or not, but I'm you know you're going to find creepy people who just want action and be done. So, like, how do you sort through that?

Ilana Dunn:

That's really hard. I mean, a lot of apps do allow you now to put your intention, like what you're looking for, on your profile, but even still, someone could say they're looking for a relationship and be the least emotionally available person in the world. I think the most important thing that you can do and this is scary for people to do because they don't want to be too forward, but on a date on your first date, second date at the latest there should be a conversation about what you're looking for. Because, let's say, you are hitting it off with somebody on the first date. It's like the best connection ever, but you don't want kids and they are dead set on having multiple kids.

Ilana Dunn:

The two of you have no business being on a date with each other. You're just putting yourselves in the position to waste your time and get hurt and avoiding that conversation of like, what do you want in life? What are you looking for? If you have, the longer you avoid that, the more hurt you're going to be, the more difficult it's going to be to end it, because then it's like you're five dates in. You finally talk about it. Well, it's been a month. You've already built up this connection. One of you, if not both of you, is going to think oh well, maybe I'll convince them.

Ilana Dunn:

And that is not a situation you want to be in.

Jonathan Merel:

Oh and that's I mean that's crucial to get out information like that. You have to get that out first or second date. What's even crazy is I've there are people who go into marriages that don't know this information. There are people that go into marriages and then leaving the idea of kids or no kids up in the air, which is just a disaster If someone wants them and then someone doesn't. I mean there are people who like don't even discuss, like political beliefs, and then they find themselves so at odds and then like that causes the breakup.

Jonathan Merel:

These are things you should talk about Date one, date two, and don't get fucking married and then decide it and like here you are saying, get this out of the way on date one, date two, and people are actually getting married without talking about this stuff. So yeah, that is so crucial. I mean, are most people going to be truthful when they talk about that or are they just going to kind of? I mean, obviously you'll find out down the road if they are or aren't, and that's, of course, something you'll figure out. But again, you would hope, think people would be truthful about these things and get it out of the way if they're really serious about finding someone for a serious relationship.

Ilana Dunn:

You know what I do think that we're all at a point where people are exhausted, Everyone who's dating is so burnt out and exhausted and they don't want to be dealing with somebody that they shouldn't be dealing with. I think what could happen is somebody might say oh yeah, I'm looking for a relationship with the right person, so if I find the right person, then of course I would want that, and so that the other person here is okay, they're looking for a relationship, I could be their right person. And then they get down the line and that person is not looking for a relationship with them.

Ilana Dunn:

You know, I got into this position so many times where I things would start off really great. We would go on dates, we would start hanging out more and more and going and meeting each other's friends. I even got to the point with somebody where I met his family and then I'm you know, in my head I'm like, oh, we're dating. And then we had a conversation and he was like, yeah, I'm really not looking for anything serious right now. And I'm like, okay, well, I've met all your friends, I've met your family. I'm like basically like living at your apartment at this point and in my head I'm like basically like living at your apartment at this point and in my head I'm like, okay, you know what, it's still early, Maybe he doesn't know me well enough to know that he wants a relationship with me yet.

Ilana Dunn:

Okay, that's fine, I can stick around and wait and convince him. And we do that because we're so afraid to walk away from something, because it's like, well, we found someone we connect with. We've already gotten this far. We found someone we connect with. We've already gotten this far. We're just going to, you know, push down our fears of like, well, they actually don't want a relationship. In my head he's like well, he's saying he doesn't want a relationship, but he really likes me, so he likes me Okay.

Ilana Dunn:

Green light, we'll get there, and so that's part of the problem is, even if someone is telling you the truth, we don't always want to hear it.

Jonathan Merel:

Right, so you mentioned like green flag. Obviously, things that I always think are like the mark of like a good person is like do they have good family, like what's their family relationships? Like what I also always thought is like, do people have like long lasting friendships, like people who are still friends with, like their, their buddies from like kindergarten and grade school, like I think that's like the mark of a good person, someone who's had long lasting friendships, I think translates into usually like a good person or partner. But like, give me some green flags, red flags in your experience. Like just like someone who's just going out into the dating world. I mean, what are things that you think about people should be looking out for that are good or bad?

Ilana Dunn:

So I actually I've thought a lot about red flags and green flags, because the internet has gone crazy with the concept, calling out like oh, they wear socks with shoes, red flag or they wear jorts red flag.

Ilana Dunn:

I think there are so many superficial red flags and green flags out there and what matters is how they treat other people and how they treat you, and I think, most importantly, the biggest green flags are paying attention to how you feel. Do you feel comfortable with this person? Do you feel like you're talking to a friend? Green flag. Do you feel more anxious than you were before you met them? Red flag. Are you going about your week in between dates staring at your phone, desperately waiting for a text to pop up from them? Red flag. Are you able to text them first and say like been thinking about you, like what's your weekend, like I'd love to see you? Green flag. I think really honing in on how you feel with this person is the most important, because if you feel like so much anxiety of do they want to see me again, like what? How did they think the date went? You're not actually secure in this situation and more time with this person is probably not going to help that.

Jonathan Merel:

Right, that's a great point, because red flags and green flags are different for everybody. At the end of the day, if you feel comfortable, if you feel love, if you feel like a good connection and obviously if that person feels the same, that's what you want to feel. It's not necessarily this or that, or you know he did this or she did that. It's obviously, like you said, connecting to your emotions, which I think is a great point. That people maybe you know society makes them think twice about this or that. But I mean, at the end of the day it's subjective how do you feel about things, Not necessarily how you're supposed to feel. So that's a good point.

Ilana Dunn:

I was the most anxious single person ever Like it was insane when I think back about how anxious different people made me in different ways. And when I met my husband you know I think it's interesting we actually we matched multiple times on hinge over a year and a half period before we actually ever went out. We never spoke until the third time when we actually made a plan.

Ilana Dunn:

But our first date was fine. I used to leave first dates thinking, oh my God, I'm in love, I'm going to marry this person, and that not a good sign. You should not walk away from a first date saying I'm going to marry this person because you don't know them yet. And so our first date was very fine. It was like a good first date. But I left thinking like, oh, I won't die if I don't see him again. Our second date we got to know each other better. It was good. Good enough to get to the third date. And our third date was the morning after I got my first COVID vaccine.

Ilana Dunn:

I felt so ill, like I had a fever. I couldn't lift my arm. To get ready for this date, I had to make like a fake sling for my arm because I couldn't move it and I felt horrible. But I didn't want to cancel. He had taken off work to take me on this date, which was, I thought, like, oh, maybe that's too much. But in hindsight that was really nice. We all want someone who's nice.

Ilana Dunn:

This is someone doing something nice and on a day where I felt so terrible, like physically and emotionally, I had so much fun. We were just supposed to get brunch. We ended up getting brunch. We ended up walking around the city, we ended up going to a bar where we both used to live but didn't know each other at the time.

Ilana Dunn:

And at the end of the day, I was getting in a cab to go home and I was like you know, I'm just going to go sit on my couch for four hours and watch One Tree Hill. You're welcome to join. He came back. I felt so comfortable to like change into sweatpants and a sweatshirt in front of him and we just laid on the couch watching my comfort show for four hours and at the end of the day, I was like wow, this is somebody where, on a day where I felt my worst, I was able to have fun. I was able to be so comfortable in myself and I had no fears of like is he going to judge me for any of this? And that was a huge green flag for me. This just felt like hanging out with my best friend all day.

Jonathan Merel:

Yeah, Well, that's what you want to feel, that's great, and the rest is history. All right. So now we got okay, we got the dating. You found someone. This isn't necessarily just you, but like what are things people should think about to keep the flame going? Obviously, you're kind of in your mode. You're going forward, whether it's dating, whether you get married, whatever it is. You found the person and now you're in the relationship. You're cruising down the road. There might be some bumps in the road. How do you keep the flame going? How do you keep the flame going? How do you keep the excitement? How do you keep the relationship going in the positive direction and getting through those little bumps in the road?

Ilana Dunn:

I think the most important thing when it comes to keeping the relationship going in the right direction is communication. I think when we are afraid to say something to someone, like those hard conversations are the most important ones to have, and the earlier you bring it up, the easier it's going to be. Because when you don't talk about your concerns or your fears, or we just moved in together and the way you organize this thing is not working for me something as little as that if you don't talk about it, it becomes this thing that you're holding on to this, like anger and it builds resentment, and then it becomes a big thing when it could have just been like you don't load the dishwasher in the right way, not to say my way is right, but like let's do it my way. You know it doesn't have to be a big thing. It can just be like oh, I noticed we like do this differently, like let's talk about it and come up with a way that works, and so I think really just not holding things in and feeling like you can talk to your partner, and again like it might be a bigger conversation than the way you load the dishwasher. It might be something with family, it might be something with work or anything. You just got to talk about it openly and honestly. Work or anything you just got to talk about it openly and honestly, I think in terms of keeping the excitement going, really remembering like how did you feel in the early days and what were you doing, of course, like the honeymoon phase, like that's amazing and you're not necessarily going to get that back, nor, in reality, can you live like that your whole life. But keeping traditions going.

Ilana Dunn:

Jake and I both love the show the Bachelor, and on the Bachelor they give date cards to people and they plan surprise dates for each other, and so Jake and I started doing that early on and we still, every few months, we'll surprise each other with a date card day, and it's just something like so simple that all it takes is a little thought and effort, but those are the dates that we enjoy the most, that make us feel like so connected to each other, and it's something we are going to do for the rest of our lives.

Ilana Dunn:

We did them on our honeymoon, we do them now and I also think, just making sure to like have fun. You know, dating turning into a relationship, turning into a marriage life gets hard. Making sure that you can have moments of fun and maybe it's fun is even just sitting on the couch playing a game, maybe fun is just watching a show together but separating it from your daily life. If you have kids and you're struggling to find a date night as much as you can, even once a month or after the kids are to bed, it's saying let's make this a date, separating the day from the date and putting the intentionality into it. Even if you can't get a babysitter, you have to do it at home. You can find a way to make little things big things, and I think that's been a theme throughout. My relationship, too is like it really is the little moments and the little things that are our favorite.

Jonathan Merel:

That was a great answer. Even going back to the communication part, I mean, as divorce lawyers, you know we refer people to marriage counselors all the time and obviously talk to them ourselves and marriage, marriage counselors if you, communication is always the number one priority. When you get in a rut and, you like, communication breaks down, like you said, the littlest things start to fester, that turn into big things, that turn into marriage breaking things, that turn into really bad things and if you would have just talked about it from the beginning, it would have gone away. But I think that's kind of what happens with marriages. They just they lose their way. They lose their fact that they used to be in love with each other and could talk about anything and now, you know, are so upset about things that they compartmentalize it and keep it inside and internalize it. That prevents them from communicating, which often leads to the breakdown of the marriage.

Jonathan Merel:

So I think you nailed that completely and your other answers were awesome too. All right, so we're on relationship mode. Not everything is a happy ending and we've got breakups, and I know your podcast talks about breakups. How to navigate that? I guess my question is what's the best way for someone who just experienced a breakup, whether after a short relationship, a marriage, whatever, to kind of emotionally reset and get in that mindset where you can move forward. What's your advice when it comes to that?

Ilana Dunn:

I think first of all, after getting broken up with or going through a breakup, give yourself time. We put so much pressure on ourselves to get over it and move on, and you know, oh, to get over someone, you got to get under someone else. That might not work for you. You might actually need a week or a month of prioritizing yourself, crying every single day, journaling, therapy, whatever it is, and that's okay. This is a huge life change. You're not only mourning the relationship or the marriage. You're mourning the future that you thought you had, and so there's a lot to process and to digest, and it might take two weeks, it might take two months. For some people it might take two years, and that's okay.

Ilana Dunn:

I think the biggest thing is don't rush it. Talk to the people in your life. We are sometimes so afraid to cry in front of certain friends or really open up to people, but everyone around you wants to support you and wants you to be okay, and sometimes they might not know how. Maybe a friend is encouraging you to go out when all you want to do is sit on the couch and cry. They're encouraging you to go out when all you want to do is sit on the couch and cry they're encouraging you to go out because that's what they think you need. They don't know what you need. They'll only know if you tell them.

Ilana Dunn:

I think it's really smart to kind of fill those gaps. You know, you had this person who you would go to dinner with, you would watch shows with you, would text when you had a random thought during the day, you would go to workout classes with your partner may have been your everything, and so I think, assigning different people in your life, whether it's friends or coworkers that you're friendly with, and saying all right, you're going to be my sushi person Every Thursday, let's go get sushi. Okay, amanda, I'm going to text you when I have a random thought. You don't even have to respond, just know that I'm going to text you when I have a random thought. You don't even have to respond, just know that I'm going to text you for that. Alex, we're going to go to workout classes. I know you like working out. I need someone to keep going with me, keep getting me there. And it's okay to tell your friends hey, I'm picking you for this thing. They want to support you.

Jonathan Merel:

The best way for them to support you is for you to tell them how they can. Yeah, and I think that's important, because people you know can become just kind of I don't know. They can kind of curl up in a ball and not want to talk to anyone. I think it's really crucial to use your support system and obviously, again, if you have good relationships, if you have good friends, if you have long lasting friendships, these are the people you should rely on for your support and you know they will support you. If you just kind of curl up into a ball, that's when it could really get ugly and people get depressed and it's kind of hard to come out of it. So, again, I think you hit the nail on the head.

Ilana Dunn:

Yeah, and if you do have to curl up in a ball, curl up in a ball with a friend next to you. Exactly.

Jonathan Merel:

It can really be emotionally traumatizing. You just don't want to go down that dark path. Reach out to people, don't be scared to see a therapist, obviously. Thankfully, therapy doesn't have that stigma that it used to have. It's like the cool thing to do now, even where before people were like God that person's in therapy. It's really not like that anymore, which is great, because therapy is great for anybody, whether you have problems. You don't have problems. You're in a relationship. You're just out of a relationship. I think it's really helpful.

Ilana Dunn:

Absolutely. And to answer your initial question of like, how to, you know, prepare yourself to get back out there? I think once you do feel like you are getting to a better place, you know, you'll know your mind will tell yourself when you're kind of ready. You might see somebody on the street and be like, oh, that person's kind of cute, or you might like have an urge to talk to someone. Or you might just say, like, I kind of just want to. You know, get on an app, get my profile ready, see what's out there. That doesn't mean you have to go on a date tomorrow. It's baby steps and I, even after a breakup, experienced something where I did that.

Ilana Dunn:

I dabbled, I made my profile again, I started over time messaging people and a few weeks later I got into a great conversation with someone. He asked me out. I said, okay, we went on a date. It was probably the best first date I ever had. We went on another date, we went on a third date. I was crying before and after every single one of these dates. I was crying about my ex and I ended up after the third date. I said to the guy I do think there's something here. I really like spending time with you. I know I told you I recently got out of a relationship. I didn't really tell you how recent it was and I do want to, you know, keep getting to know you but I thought I was ready to date and I'm not, and he could tell it was honest, it was real the way I articulated it. I didn't, you know, just say I can't do this anymore, Like I was. I was genuine about it and we ended up becoming great friends.

Ilana Dunn:

Yeah, and then I took a break because I wasn't ready, and that's okay.

Jonathan Merel:

See, I think the reason why you're so relatable is you are real, just like that example. You tell it how it is. There's no secrets. You are who you are and like you or not. That's, I think, why you're so popular, and I mean this has been so fun. We've literally covered it all, from relationships to dating, to keeping things going, to breakups, to how to keep yourself sane in this crazy world we live in. Whether you're single or married, or about to get divorced or divorced, whatever you are, you're such a great resource. I think all my clients are going to love this. I can't wait to publicize this on LinkedIn and all of our social media stuff. I want to thank you. Tell our audience what's the best way to find you on the podcast and social. Tell us how do we find you.

Ilana Dunn:

Yes, thank you so much. If you want to find me, I'm pretty easy to find. I'm at Ilana Dunn and at Seeing Other People, and you can listen to Seeing Other People wherever you get your podcasts. And stay tuned, because we're going to get Jonathan on.

Jonathan Merel:

Woohoo, this was awesome. Thank you again. I can't wait to go on your podcast. I'll be super excited and this was amazing. Thank you for coming in. Thank you, this was so much fun. All right, that's a wrap. Woohoo.

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