Online Dating After Divorce: The Most Common Dating Profile Mistakes


Alyssa Dineen, author, personal stylist, dating expert and founder of Style My Profile, is helping the online dating pool one person at a time! She gives us tips and tricks on everything online dating from curating the perfect profile to making the best first impression. 


  • Curating the perfect profile is all about resonating. Use all the photos you can and make sure to showcase your personality and sense of humor. 
  • Online dating is hard for everyone and burnout is real! Don’t beat yourself if you’re unsuccessful at first. It takes time. 
  • Seek advice about dating. Find a coach and a community! Remember, you are not alone.




Welcome to another episode of the exEXPERTS DIVORCE etc… Podcast where we give you all kinds of information and tips on everything divorce. Why? We’ve lived it, so we get it! We’re Jessica and T.H.

Jessica: Okay, so now let’s get into the podcast today. We’re really excited to be talking to Alyssa Dineen, a personal stylist and founder of Style My Profile where she helps you with everything online dating. Plus, she’s the author of the upcoming book, The Art of Online Dating. Welcome, Alyssa, thanks for being here.

TH: Welcome.

Alyssa: Thanks for having me.

Jessica: I really just want to start off with the Style My Profile because initially when I first heard about you, it turns out it wasn’t at all what I thought it was going to be. It’s such an important service for the millions of people out there who are actually online dating. Can you give us like a quick rundown of exactly what it is?

Alyssa: Yes. We help people with like you said, everything online dating and revamping your style, basically, when you’re getting back out there into the dating world. We do everything from shopping and styling, photos for your online dating profile, we write your bio for you, we do a lengthy discussion call and then write your bio for you, and now I also do date coaching. It kind of evolved over the years, but it originated as a styling and photo service for online dating, but it’s definitely evolved since then.

Jessica: Tell us a little bit about how you got involved in it. You had been married, and you’d been divorced. How did this come about?

Alyssa: I had been with my ex for almost 20 years. We met in college, but way before any kind of online dating or even cell phones [computers]. I was 41 when we got separated, and I think I had mentioned before that I got set up one time on one blind date by one friend. You think that you’re going to get set up by all these–that every friend you know is going to set you up with some divorced friend of theirs, but that happened one time and–

Jessica: I don’t understand why nobody knows anybody, but that’s a whole other–Alyssa: I know. I know. My theory is that everybody’s afraid what if something goes wrong or…I don’t know. Who knows?

TH: That was the only time I got set up, it was a disaster. But there was an ulterior motive on the other side, so I walked right into that trap.

Alyssa: Oh no! God, I would love to hear that story sometime. But anyway, mine wasn’t a disaster. It was just uneventful and didn’t work out. Then I realized pretty quickly that I had to go online, and I really had no idea. Like most divorced people who have never online dated, I had no idea what I was doing. I kind of used up all my asks to this one single friend I had. I was bugging her constantly and asking her advice on everything. I was like I just have to figure this out on my own. It took me a few months to figure it all out, not that I figured it all out, but I at least figured out what photos to put on there, and what to wear on a first date. I eventually got to realize what to write on a bio and of course, the messaging aspect of it is like a whole other beast, as you both know. That took a little bit of practice. I met my partner on Tinder after a little over two years of online dating. When we met, he’s also divorced and had never online dated either, we’re just comparing stories about how clueless you feel, first of all, being a divorced person getting back out there when you married your partner way, way before all of that happened, and then also just sharing stories about how you see so many profiles that could use a lot of help. It’s interesting how you think why isn’t anyone at least asking an opinion of somebody like a friend?

Jessica: It’s crazy some of the shit you see out there. I’m like are you for real?

TH: But Jessica, you and I helped one another with our profiles, for sure.

Jessica: But that’s what I’m saying. But at the same time, it’s like some of the pictures that people put on there are crazy and some of the stuff they write.

Alyssa: Yeah. I think that there are women like you guys. I did ask. I would show a profile picture here and there like, should I put that up there? But your friends who are married don’t get it at all. They’re like, sure, that’s a great picture. Really, you have to be in it to really get it. But then also, so many, specifically men, I feel just don’t even think to show their profile to somebody. They just don’t. Maybe people under 30, maybe they show each other, I don’t know, but nobody thinks to show anyone. These photos that are put out there, I’m talking to my partner about it, he was just saying even some of the women’s profiles were also in need of some help. But originally, I was thinking I’m going to help all these divorced men who are newly in the game and need help restyling themselves and figuring out what photos to take and what photos to put on there. But it’s interesting because I feel like especially the first year it was almost all women who were coming to me. What that told me is I felt it was women think to get help with things. I think we just naturally think I don’t know how to do this so I’m going to hire someone who does. I think a lot of men are just, oh, I’ll just throw up a few pictures here that I had from the last 10 years ago and off we go, and I’ll write a few words down. I just found it so interesting that so many women were coming to me wanting to improve their profile and got that they needed help, but it took a while. I did market it towards men more. Now I actually have quite a few male clients too of all ages. Yeah, it was an interesting way that it shifted around.

Jessica: Helping the online dating pool one person at a time.

TH: Totally. I feel women are more afraid to make a mistake also. They’re going to question how they’re putting themselves out there. I’m a marketing person, so it’s all about building your brand, right? Yeah. What’s my brand to the world of potential suitors? I was homely then, now I want to be like a little sexy and a little fun. What sends that message out there? My boyfriend now, it’s funny because you’re talking about the pictures, it’s also what pictures resonate with certain people. He had one picture of himself that doesn’t look like him. He was all clean shaven, and he’s got scruff. The other pictures were of his legs crossed on a boat with a beer, and I saw the tattoo on his leg. His ski boots crossed with a beer on a ski mountain. I was like,

I like to ski.

Jessica: I like to drink beer on a boat.

TH: And he’s pretty cute. I’m good to go. I didn’t even need that much. Honestly, we met on Hinge which was new at the time. But what I liked about Hinge, and Jessica helped me because at first it was boring, they give you the prompting question so–

Jessica: Now they all do that though.

TH: But back in the day three years ago, it was the new thing. It helped me the three things what, you know, two truths and one lie. What resonates with people, even if you don’t have great pictures, or whatever, it’s kind of funny what resonates and what doesn’t. Those two pictures without his face are like, oh, I want to be there. I want to do that with someone. He is very handsome, but it’s not always a picture of yourself. He looked at my pictures and was like those are not great pictures. One of them was me climbing something in a skort, a fanny pack, and my glasses like I’m an outdoor and go-getter girl, and that’s who I am. He was like that was my least favorite picture. Well, he still liked me, and now we’re three years later, so we’re good.

Alyssa: Yeah. I think as long as you have a couple of photos that, as you said, resonate with somebody, that’s really all you need.

It’s even just a couple of photos that really strike someone. Because with my boyfriend too, I say this in all my interviews, he had one good photo, and luckily, that was his first one. The others were horrible. I really was like hmm, on that one photo, and then the rest, I was like ugh. Then I was like, I’m just going to go ahead and swipe. We met the next day, and the rest is history. There’s a long story behind that too, but we met right away, and definitely there was a connection. My point is I think even if you can just pull together just a couple of great photos, it really does make a difference. The other one piece of advice that I tell everybody is so many people make the mistake of only putting one photo on there, and it’s still unbelievable how much that still happens. You think that you just do a quick Google search and anybody can find out that people are not going to swipe on you if you only have one photo, but it is especially I would say with people 50s, 60s, and older, that’s super common.

Jessica: I want to know what would you say are the three biggest mistakes that you’re seeing people do on dating apps, whether it’s the type of picture: selfies, guy with a fish, girls and bikinis, whatever, or not using enough humor in their profile or whatever. What are the three biggest things that people are doing, and they don’t even realize?

Alyssa: The list is endless, but–

Jessica: Okay, the top five things?

TH: The most popular.

Alyssa: Aside from the doing only one or two photos? Well, the other big one is, and so many people still do this too, is doing a range spanning like a 10 year timeframe when it’s so obvious to everybody looking at your profile that the you there is not current. I feel that already makes people feel a little bit like, uh, I don’t know, I mean, why would they be putting up these old pictures?

TH: Right. You’re not trusting already.

Alyssa: Yeah, I feel like that. Definitely even worse than that is just putting older photos of you, and maybe you have aged a lot, maybe your body type is totally different now. You’re only doing a disservice to yourself by doing that because you show up on a date and you’re 10 years older, or you’re 40 pounds heavier, or whatever it is. Maybe there would have been a connection, but immediately the person’s put off by that and the door closes.

TH: It’s a bad first impression.

Alyssa: A very, very bad first impression. I had a client who was putting up all these photos of herself where they were either old or certain angles, and it was definitely painting her as a lot younger than she was. I had to really talk her into it, but she was she really was sold on the idea that I just want to get these people to match with me and message with me, then once I meet them, it will be my personality.

TH: I’ll sweep them off their feet.

Alyssa: But what I was trying to tell her is you’re going into that date, and the first thing people think to themselves is you look nothing like your photos. Some people really have a hard time getting past that. But obviously, as you guys know, you have to be honest. You have to be open. You have to put your whole self out there because otherwise you’re wasting your own time.

TH: There is actually, before you get to your last tip, I remember because I’ve met many guys, most of them on Match. Hinge was new for me, but there was this super good looking, hot, and extra stylish– he looked almost too good to be true, which was the case. He put his picture up there for his friend’s profile because he knew his friend wasn’t going to get any hits with his picture. His friend was like six foot seven, just whatever. When I liked it, he goes, “Thanks for liking me, but I just want you to know I don’t look like this. This is what I really look like.” That bait and switch I also did not like, but I knew that that was happening.

Alyssa: Well, and I’m always curious who is going to respond to that?

TH: Right, someone who’s desperate.

Jessica: I want to get back to your tips, but it’s interesting because I feel most of the dates I go on, more than most, the guys are always like, wow, you look just like your pictures. I have found that at least 90% of the time that I’ve gone out, I think also that the guys look like their pictures. But from having discussions with both women and men, it seems like women are, whatever word you want to use, not forthright about the pictures that they use, or they’ll be crazy filtered, or whatever it is so that the guys don’t like think that they look like their pictures.

But for guys, I find that they’re often exaggerating their age. Maybe it’s because of the age I am. I’m 49, so I feel like they’ll write that they’re whatever, and then somewhere on their profile it’ll be like, ‘I’m not really 48. I’m 54.’ Then I’m like we’re done.

Alyssa: I know. I would say you’re right about that. I think that’s way more common for men.

Jessica: It’s so interesting. You’d think that women would be the ones to be lying about their ages.

Alyssa: I know. I know.

TH: But women are filtering themselves so much. I feel women are more concerned about the way that they don’t look, and men are more concerned about their age. Is that a true assumption?

Alyssa: Yeah. They’re way more concerned about their age.

Jessica: But part of it’s because of filters. They know that women will filter up to 50, so they don’t want to write that they’re over 50.

TH: Right. They’ll be out of the game.

Alyssa: Well, also a lot of men, I hate to say this, but I work with a lot of men, they really do believe that they should be with somebody much younger. They all say the same thing, “But I’m a really young 60, a really young 60. Most people think I’m only 50.”

Jessica: You’re like, get over yourself.

Alyssa: Then have people be pleasantly surprised when they meet you. They’re expecting a sixty year old and you look like you’re 50. That’s awesome. Just do that. But it is hard to convince people that you’re right.

Jessica: Be your true self.

Alyssa: I’m probably still doing this that I know what I’m talking about.

Jessica: What are the other mistakes you see people making?

Alyssa: Well, definitely for bios, either writing a resume as your bio. That’s pretty common I think, especially for people in their 50s, 60s, 70s. Then like you said, I think it’s really important to have something either quirky about yourself or something funny, or funny like an anecdote, something that’s going to get people’s attention. Because you know, after looking at profile after profile after profile, you see the same things written over and over again. My joke is if I see, ‘I’m loyal, kind and funny’ one more time, those three–

Jessica: Right. I want to laugh and have a good time. So does everybody.

TH: But then you have the other people who are spilling their guts. It’s like a book. I don’t want diarrhea of the mouth. I want short and sweet. Tell me what you what you think you are. Tell me what you like to do. If I like to do those things, and I like those things about you–but I feel like it’s paragraphs and books, and those are out.

Alyssa: Yeah, you just save something for your date to talk about. I think especially with Match where you really can go on and on and on, and OkCupid, back when I was dating, I did that too. You really can write a whole book practically. I agree with you. Shorter is better is definitely better.

Jessica: But if you can make someone laugh.

TH: There’s got to be something that makes you memorable.

Jessica: There was a profile that I remember seeing and I wasn’t really interested overall in the profile. He had very little written in it, but the last line was something like, ‘I started a COVID garden, so there’s that.’ It made me laugh. I was like too bad I’m not interested in the rest of his profile because that’s fucking funny.

Alyssa: Yeah, that is really funny. It’s just that one little thing. I agree with you. I definitely went out on dates with guys that maybe I wasn’t super excited about their pictures, but when they write something really funny or interesting, that made me want to go out with them. That definitely I think is really important.

TH: Yeah. I have another question. What about with kids?

Because I remember looking online dating, and I didn’t really love it when people posted pictures of themselves with their kids, or even just their kids. For me, that was a turn off. And primarily younger kids, I felt like, I need to know you. You said you have kids in the filter, because for me also, my criteria was you had to have kids otherwise it wasn’t going to happen. I’ve got three kids. But what is your advice for people with kids as far as your dating profile, other than indicating you have kids? With pictures and in the bio, what kind of guidelines do you have?

Alyssa: I get asked that a lot actually. I think it used to be more taboo than it is now to include your kids in your profile. I always say, if you want to include one photo of you and your kids that’s fine, but I don’t think more than that because you want people to realize that you have a life outside of your kids. It’s fine if you want include one photo of them. I think especially now when pretty much anyone can Google anybody and find [all their pictures], they really can see anything. It’s not so private anymore. I think that having one picture is fine, but I really recommend not more than that.

Jessica: Thank god, I only have one on my profile.

TH: I knew you’d have one. I do the same for me.

Jessica: You can see my kids’ faces. I’ve actually had conversations with guys that I’ve met on apps who have asked me what’s the mindset behind the fact that I’m showing my kids faces versus blurring them out. A lot of people will blur out their kids faces.

TH: But if you blur out your kids faces, isn’t the whole point to show that everybody’s happy together? Why show the picture if you’re going to blur it out?

Jessica: I don’t know.

Alyssa: That’s exactly right. Why have the pictures in there if you’re not going to show their faces in it?

Jessica: Because I don’t know, you’re a dad or you’re a mom. But I’ve had people ask me, and the answer I think is no, I’ve had people ask me if my kids know they are in a picture that I have on my dating profile.

TH: And?

Jessica: I don’t know that I ever told them. I don’t really care.

Alyssa: Unless you live off the grid in Maine or something, pretty much everyone has some sort of a public profile in some way.

Jessica: Right. People can see my kids in other places.

Alyssa: Yeah, exactly. As I said, it’s just not as important anymore to hide them away.

Jessica: The bottom line is I think that so many people, as in your experience, because you have a successful business doing it, so many people just don’t know what they need to know when it comes to creating a great online dating profile. It’s such an interesting service that you offer. It’s so great that it’s available and out there, because so many people need to utilize it. People really need to utilize it.

Alyssa: They do. Even taking it one step further than just the way your profile looks, you know this, I mean, there’s major burnout from online dating.

That’s what I was realizing. I was working with people and I’d get them all up and running, and they’d be all excited, and their profile would look great. They’d have some new outfits, and they’d be feeling really good. Then I’d hear from them a month later and they’d be like, oh my god, this is this is horrible. This is not going well.

TH: It’s a job.

Alyssa: It’s a total job, and really, it’s helpful to have a coach. Just like you’d have a business coach or therapists or whatever it is that you have, I feel to even keep you motivated to stay out there first of all is huge. But also, I think validating all the stuff that happens–I’m not going to swear on your podcast.

TH: You can though. We do.

Alyssa: Okay, good. There are just so many weird crazy things that come up here and there. Everybody’s experienced something, I guarantee you almost just like that. My feeling is just creating like a community around it like, what you’re experiencing is normal. Having burnout is normal. It is tedious, it is monotonous, it is sometimes annoying, and it is sometimes painful, but it’s also fun. It’s also exciting. It’s also how I’ve met some friends from online dating. I’m still friends with some of the guys I dated. It’s people that I never would have probably met otherwise. Anyway, I feel having the right attitude going into it, which is why I talked about intentional dating, if you follow me on Instagram, it’s really being mindful and intentional about it and not just checking your app once a month and thinking that you’re going to get dates that way. It just doesn’t it doesn’t work that way. It really doesn’t. I used to work with a lot of models doing fashion shoots and everything. When I first started online dating, I was still doing a lot of shoots. It doesn’t matter what you look like, everyone’s having the same issues as you are. You still get blown off. You still get ghosted.

Jessica: Didn’t you just see those two videos recently that went viral online? One was of Ben Affleck and one was of Matthew Perry, I think. But the Ben Affleck one was like he had met a girl on Raya and she unmatched him. He sent her a video message and was like, why did you unmatch me? It’s me. It’s like even Ben Affleck–

Alyssa: That’s really hilarious.

TH: I remember that. That was funny.

Alyssa: No, and it happens to everybody. I think when people hear that, they feel not alone. They feel like this is all normal and it’s all part of it.

TH: Do you ever have people come to you and they’re like, listen, I heard about you. I want to get out there. I want to be dating. Do you do any kind of an interview process of your potential client to make sure they’re ready to be dating and do prep work? This is totally a general statement, but in my experience, first you’re on a tear and you’re super needy for a bunch of different things. There’s no agenda, and you’re just like an unleashed wild animal.

Alyssa: It sounds very familiar.

TH: I’m saying this for a friend, of course, not myself. Then you start to calm down, it’s like stages of grief. There has to be stages of getting back into dating. What are those?

Alyssa: Well, my journey was definitely similar to your friend’s. I was. My friends all made fun of me because I just couldn’t get enough out there. I was like, oh my god, I just want to go out with everyone.

TH: I was double booking dates in a day. I was assigning cities, and if he has hair, or he’s bald, or he’s tall or short, he’s got a kid, he’s got a dog.

Alyssa: Yeah, no, totally. Not everybody does have that journey though, which is interesting. A lot of people are really slow burners. They’re dipping their toe in, and then they get a little more excited, but they’re really hesitant about all of it.

Really, it just depends on who I’m working with, but there’s so many different stages that people go through. Some people don’t go through that tear stage until like six months in and then they’re like, whoa, now it’s really happening.

TH: This is awesome.

Alyssa: But there are definitely people that aren’t ready for sure, and I can usually tell that pretty quickly. I always have a 30 minute discovery call where it’s a complimentary session and I’m able to tell them more about what I do. There’s a type, it’s usually younger guys, and they’re like, late 20s, early 30s, who want to hire me, because basically, they just want to meet hot women. They literally say that. They’re like, I’m not meeting enough hot women online, and I want you to make my profile look amazing, so that I meet all these hot women. I’m like that’s great for you, but that’s not what I do. Not that I’m only working with people that want relationships, but I work with people that really want something more meaningful than just getting somebody hot.

Jessica: Fair enough.

TH: So you would say, ‘I’m not the right person for you. Come back to me when you’re looking for a little more’?

Alyssa: Yes, exactly. That’s only happened to me a handful of times, but usually when people come to me, they are ready. They’ve already been out there unsuccessfully. And sure, having great photos, having some well-styled photos, and a more curated profile helps for sure to get matches, but it’s so not just about that. It’s also about like connecting with people by text, which is really hard, and it takes practice, practice, practice. Just all of it takes practice. Even taking a selfie, I don’t know if you guys when you first got divorced, I didn’t even know how to take a selfie.

TH: I am not good at that.

Jessica: I heard that you’re not supposed to post selfies on your profile usually.

Alyssa: Well, it depends on if it’s good or not is my theory on that. There’s definitely plenty of selfies that are well done. I think you just have to practice at it. I always say don’t put up a selfie until you’ve tried it like 500 times because it takes a long time to get the hang of it.

Jessica: On that note, I think we’ve got to wrap it up. There’s still so much more to talk about. We’d love to have you back because I think diving into the online dating game, that’s where everybody is. If you haven’t done it, you have to do it. Really knowing the right way to do it is essential. As you said, once you meet someone then it’s on them, the connection and your personality. You can’t have this great profile and then you’re a dud in person. Thank you so much today for today.

Alyssa: Yeah, thanks for having me.

TH: Alyssa has a book coming out in October. We’re going to do a follow up podcast with her to dig deeper into it, but why don’t you give them a little teaser?

Alyssa: It’s called The Art of Online Dating and it’s being published by Harper Horizon. Basically, it’s anecdotes of my own experiences, my clients’ experiences, of course all names changed and everything, mixed with prescriptive advice. It’s really like a how-to meets a fun, funny memoir type thing. It’s definitely going to get people laughing. Hopefully it will get people out there dating. I’m really excited for it to come out.

Jessica: That’s awesome.

Alyssa: Yeah, I would love to come on again. I can talk more about that too.

Goodbye: For everyone out there listening, if you know anyone at all who would benefit from what we talked about today please share this episode and everything exExperts.  Be sure and click to subscribe to the Podcast on iTunes or wherever you listen to your podcasts and please follow us on social media @exEXPERTS Divorce etc… on Instagram and Facebook and YouTube and our website at  Thanks for listening!

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