Insider Tips for Dating After Divorce




Jessica: Do you wonder what men are thinking when it comes to dating post divorce? Wouldn’t you like to know how to approach finding a new partner and the way that men will respond and relate to? Do you want to hear from the woman who works with men and knows how they think about all of this? Well, that’s exactly what we’re talking about in today’s episode of the Divorce etc… podcast. We’re the exEXPERTS, Jessica and T.H. We focus on helping you navigate your divorce and successfully moving on with your life. Please follow us on all social media at exEXPERTS, and check out for tons of free divorce related resources. Let’s bring in today’s guest.

T.H.: Hey, everybody, it’s T.H. here. We have Celeste Moore with us. She is an image consultant and dating coach, and really works with both men and women, but primarily men. I’m going to start this interview not just by welcoming you to our show, but why men? What is the deal?

Celeste: Thanks for having me, ladies. It’s such a pleasure to be on your show. For me, it came over time. I have dealt with a lot of men throughout my life, and they just seem to be a little bit easier. Women would hire me, and it was this pull. It was a struggle. It was like they didn’t really want to hear the feedback that I was giving them, the honest opinion. I was like, “Well, why are you hiring me? This is this is not working for any of us.” At the end of the day, every time I would have a man client, it would just be like, “Okay, how do we get from point A to point B?” Perfect, boom, and it would just be really simple. It just feels like I can communicate with them a little bit more direct as well.

Jessica: I mean I love it because it’s a much needed service. But I’m really wondering how did you start in that, because part of me feels women are generally the ones who are more open to asking questions, more open to feedback, more open to needing advice and admitting that they need help. How did you build this business around men having to say, “I need help”?

Celeste: Well, Jessica, that’s a really good question. Because yes, typically, women are more open to coaching, more open to help. They ask for it. Surprisingly, there was a sprinkle of men that were like, “Okay, I need help. I don’t know how to dress. I don’t know how to present myself.” Typically, in the beginning, I dealt with just corporate men, lawyers, doctors. One of my first clients was presenting in front of the SEC, so he really needed to come across a certain way, say a message solely by his look and the colors that he wore. I just think that over time—another thing was the girlfriends and the wives were also like, “You need to call her. You need to set up a time.” They begrudgingly did so. But at the end of the day, they were so happy because they didn’t realize the information that they were going to receive and the tools that they were going to receive.

T.H.: But you don’t you think it’s also because men are maybe a little bit lazier and don’t want to take the time? They don’t like to shop. They don’t want to spend the time. Just fix me up. Just get me some stuff. I feel like also women want to be involved. They want a different kind of relationship out of it, right? Men are probably like, “Celeste, I have an appointment. Dress me, talk to me, coach me – I’m in.” You know what I mean? They don’t really want to be your friend. They just want you to fix it all up.

Celeste: So there are a number of guys like that, or men. There’s also once we start the process, they get really excited. They’re like, “Oh, ooh, what looks good on me? Ooh, ooh.” So they have this feedback that they’ve never had before, other than their wives or their girlfriends, or if they’re single, someone else in their life. “Oh, you look really nice. You look handsome.” But when they start learning tools on the ways to present themselves, or the right colors, or what to say if they’re single and they’re out there, like how do I get the girl, how do I go from being nervous and scared to actually being confident, right, so there’s all of these. I definitely know both of them. But I feel like once they get in to the process then there are some that are really excited. So I love that. I get really excited too.

Jessica: Help us turn this around for all the women who are listening. We may have some men out there, and you guys are going to be able to glean some tips too, but our demographic is primarily women.

Celeste: Yes.

Jessica: So what can you tell us as women that would be helpful when it comes to dating after divorce? Get us into the guys’ heads and give us the secrets.

Celeste: So the one thing that I would say for the women out there is, is pretty much the same as what I would say to men, except for some of the other coaching tools. But it’s really getting comfortable in your own skin, right? I think coming out of a divorce, I know for myself personally, I was in a very young marriage, and he was very controlling, and he was all of these things I didn’t know because I was quite young. I came out and I really didn’t know who I was. It’s really finding out who you are, like, what do you like? Maybe it’s just go shopping with your girlfriend and just try new things. Maybe our bodies have changed, right? If you’ve been in a long relationship, or you’ve been very complacent in your in your wardrobe because you’ve never thought about it really before, right? You’re taking the kids to practice, you’re doing this, you’re doing that, and maybe it’s the first time in a long time that you’ve actually were able to sit back and look at yourself and really examine where it is you want this new person to come out of. I would really recommend go shopping with your girlfriend one day. Let the kids be wherever, or if you don’t have kids, just really embrace trying new things that maybe you’ve never tried before. I mean, that’s just like one tip.

T.H.: But what are the men thinking? So if I’m out on a date—and it’s clearly everybody, we know not all men think the same, and not all women behave the same. These are broad strokes questions here, everybody. So if I’m going out on a date—I think that my very first date, I was really worried about what I was going to wear. I was afraid that he was going to see my imperfections that I was super sensitive about. My first date was actually with a crush I had from college. So it was an easy first date because I knew he really liked me then. But are guys really focused on that? Or are they focused on oh my god, she’s hot, or she’s got great energy. Are they focused on the little imperfections that we always obsess about like my neck, I got a wrinkle over my eye, my makeup’s not great, I didn’t get my nails done? Like, what do you guys care about?

Celeste: I can promise you they’re not thinking about the imperfections. I can promise you. We, as women, fret over those little things. We constantly worry about the things that they don’t even care or they don’t even notice. If we do two shades lighter in our hair color, nine times out of 10, they don’t notice, okay? So, being comfortable with who you are, building that confidence, and there’s so many different ways that you can do that. One way is just to wear a certain color, right? Red is the most confident color. Maybe you’re not feeling confident. Maybe you’re like, okay, this is really nerve racking. Let me go in, text my friend, she knows where I’m at. Just be yourself. I promise they really just want to know who you are. Yes, they’re also thinking, “She’s hot.”

Jessica: Listen, coming out of a relationship, I feel one of the huge questions for everyone likely on both sides is “Well, what are you looking for? What’s the end game?” Where do men fall, or how would you recommend women approach it in terms of are we just dating, are you just looking for some casual fun, or are you looking for a relationship? Because it could be construed as the woman coming off desperate, but sometimes you just kind of want to know what you’re getting yourself into.

Celeste: Yes, and I—

T.H.: Well, and also, what point do we even get into that conversation?

Jessica: Right.

T.H.: I mean we’re just meeting for the first time. Do women need to chill out for the first date that you’re meeting someone and just see where it takes you?

Celeste: Yes, T.H. Yes, my suggestion, man, woman, just have fun, okay? Literally, I would not choose a coffee or a wine date. One, they’re just so easy and they’re kind of boring, right? Choose an activity, like maybe you want to go stand up paddleboarding—I don’t know—depending on your demographic.

Jessica: And be in a bathing suit on my first date? Are you fucking nuts?

Celeste: You can be in shorts and a T-shirt. You don’t have to be in a full on bathing suit.

T.H.: And fall in the water? Oh my god, Celeste, these are a lot of red flags.

Jessica: What is it, a wet t-shirt contest?

T.H.: Alert! Alert!

Celeste: Okay, so pick another one. Pick another one.

T.H.: I’m thinking ping pong, bowling—

Celeste: Miniature golf.

T.H.: Hiking—

Celeste: Go-kart racing, I don’t know. Jump out of an airplane.

T.H.: Right, yes. Yeah. They’re no fail. At least you can be successful.

Celeste: Well, I always recommend trying something new because you create a bond when you go out with somebody. When you have all these good hormones from doing something physical, it’s kind of like a two folded—like, it’s just really great. Because if you’re just sitting there across from someone and you get coffee—okay, it’s really kind of boring anyway, coffee dates—but it’s just really awkward, even like getting a cocktail, right? It’s almost like you’re in an interview. The one thing men don’t want, and especially women too, is we don’t want to feel like we’re in an interview. We don’t want to feel like we’re applying for a job and we have to sell ourselves. My biggest thing is to be your authentic self, be who you are. Because nobody wants you to be like everybody else.

Jessica: Also, if you do an activity, you’re going to be able to see how they react in certain situations and how competitive they are. Can they handle the stress of something not going right or whatever?

Celeste: Yeah, are they adventurous? Is that important to you?

T.H.: Or are they fun? Do they laugh at themselves? I wouldn’t even look as far into it as you’re saying, Jess. First of all, I don’t have to talk about my divorce. I don’t have to talk about all the shit, all the baggage. We can just do something fun. Hopefully, he won’t be hard on himself, and we can laugh at ourselves and just not talk about the shit the first time. I feel like it’s always going to be an interview, “All right, what’s your story?”

Jessica: But I always to know all of that stuff on a first date. I want to ask the questions right away because that’s going to help me retrieve data for whether or not I want to see them again.

T.H.: Well, don’t you ask those questions when you’re texting initially before you set up a date?

Jessica: Some basics. But I don’t get into it too much because I want to leave some for conversation.

Celeste: Okay, you want to be mysterious. Guy, girl, leave some mystery. Nobody wants to know everything about you on the first date, or the second date, please. The more you unfold like an onion, the more the layers unfold as you get to know someone. You don’t want to give them all the big juicy bits in the middle anyway, unless you’re really, really liking each other, really vibing each other, knowing that this is going to go in the right direction. Yes, Jessica, I think it’s important to—I don’t know if you’re online dating or matchmaking, there’s got to be some process, some filter that you’re doing prior. Because yeah, you just shouldn’t go out with some random guy unless someone really knows you and sets you up on a date. But if you just meet some random guy and he’s hot, and you’re like, “Okay, let’s go out,” then you’re going to have to do a lot of digging yourself. That can come off as what you say, needy. Men don’t want to know that we want to like, “Okay, boom, boom, boom, boom, let’s make this happen. I don’t mess around.” We’re all busy mothers and have businesses, I understand that point. But when you’re dating, you really have to come into your feminine energy too. You have to leave this at the door. I mean, we’re all strong business women, right? There’s no doubting that, and we can get stuff done. But when we come to the date, we need to let that at the door. Otherwise, these two masculine energies are going to be competitive. So that’s another—

T.H.: That’s a very interesting perspective. We are just going to pause for a quick moment here. Because we know it’s hard to get honest and reliable information about your divorce and how to move on from it, so we’ve done the work for you. As the exEXPERTS, we get questions every day from people looking for a single trustworthy resource to support them through this difficult time and beyond. From the legal, the money, the kids, your self care, and all of the other stuff, we cover it all at and here on our Divorce etc… podcast. The best way to stay in touch and to hear what’s coming up next, be sure to subscribe to our weekly newsletter to hear directly from us and our exEXPERTS as we educate you on how to navigate your way to get what you need and have what you want. Just visit We’ve lived it, so we get it.

Jessica: Celeste, we’ve got to jump back to the leaving your type A personality at the door. I’m not saying I disagree with it, but I think that there may be some people listening who are like, “Fuck that. I am who I am. Why should I have to pretend to be like this soft, timid woman?” How do you explain to people how to be able to be yourself and show that you’re a strong independent woman, but like you’re saying, bring your feminine energy?

Celeste: Okay, definitely do not not be who you are. Be who you are. If you are that strong individual woman, order for yourself. I’m not saying he should do everything and you’re weak and timid. What I am saying is if he opens a door, let him open the door. Let him be a gentleman. Let him pull the chair out for you. Don’t make it a competition. Because I think a lot of times in dating, it’s either an interview or a competition. It’s like, “Oh, I did that.” “Oh, I did the same even better.” It’s really great to hear people—and men, if you’re listening, I say listen 80% of the time. Actively listen, please, and 20%, let her speak because the way that we express ourselves are through our words. I think it’s really beautiful to sit down and listen to someone. And vice versa, I mean, if he’s speaking, but don’t let him speak all the time. But you’re not weak and timid. What I’m saying is allow him to show that he is able to do these things for you. Because guys really want to do things for us, and we’re like, “Oh, I can do it.”

Jessica: What are you teaching them that are, I don’t want to say the necessities for men, but I mean, there’s a lot of debate out there in today’s day and age about what’s the man’s responsibility, particularly when it comes to like, the location, should he pick you up, does he always pay the bill, all of these kinds of things. What are you telling men are the rules, so to speak, when it comes to dating?

Celeste: So I am telling men 100% they pay the bill.

Jessica: Every time?

Celeste: It doesn’t have to be every time. For sure the first date, for sure the second date.

Jessica: Okay.

Celeste: I don’t want to say it’s old school values. It allows him to feel good about doing something. That’s another way that we show—let our feminine—even though we can. Maybe we make more money than him. Let him pay. Because trust me, that just validates him as a man. Number two, I think that you can choose. Have him give you A, B, or C of a location. I always teach my guys to pick a location closer to her.

Jessica: That’s exactly what I’m saying. I literally have women friends who are like, “I’m not going out with him because he knows I live in Brooklyn, and he chose a place on the Upper East Side where he lives.” They’re like, “I’m out.”

Celeste: Yep, I agree. The man should really be putting in more effort. In today’s day and age, they don’t really have to. I don’t know if it’s because we’re like, “We can do it ourselves,” and they’re like, “Oh, I don’t know where I fit in.” I’m trying to try and to re-educate be a gentleman. Pick A, B, or C close to her. Don’t let her struggle. It’s just a gentlemanly thing to do. The younger generation, believe me, I have nephews that are 20 and 18, and they’re like, “Why do we have to pay every time?” And I’m just like, “You have to open the door for a woman. You do that. You open her car door. It’s the same thing.” It doesn’t mean that third, fourth, fifth date, or whatever it is, that she’s like, “I want to treat you today.” Great, that doesn’t take away his manhood. That’s saying, “I want to participate in this relationship.”

T.H.: So what are some red flags that women should be aware of when they’re going out on a date, that you tell men “Do not do X, Y, and Z”? So ladies, you’re getting a heads up that if X, Y and Z happen, you might want to rethink it.

Celeste: So if there’s any type of ghosting, and I mean, you have this plan, right? You’re talking a few times, or it’s just silent. You’re like, “Oh, maybe he got busy.” Believe me, he will find time to text you if he’s into you. If there’s any kind of silence, cut it off.

Jessica: How long is the silence?

Celeste: If you had a regular type of conversation back and forth, and the pattern’s severely broken for a day or two. I mean, seriously, it’s like, if you left a text and there’s someone not responding, and it’s usually him. It’s like a kid in a candy store, “Oh, maybe I found someone else.” It could be a million things. You don’t really know, but don’t waste your time. If he doesn’t respect your privacy or anything that you feel is good for you, so that you’re comfortable on the first couple dates, if he’s just not okay with any of that, that’s also a red flag. I would make sure that he’s like, not vague enough. If he too vague in certain situations, like if you ask him a question, “Where do you live?” And he’s like, “Yeah, North Jersey.” You’re like, “Okay, duh. Like, where?” I’m not trying to stalk you, but give me a little bit of information. And he’s very vague with certain questions that maybe are important for you to feel comfortable, then that’s another red flag.

Jessica: Wait, I want to dig into that one for just a second.

Celeste: Yeah.

Jessica: Because, as a person, I ask a lot of questions. I’m not for everyone. I ask a lot of questions. I want a lot of details. I want a lot of information. That’s how I process things. Where should someone draw the line? Because I know from conversations with my friends, a lot of my friends feel the same way. That when it comes to the person’s prior relationship, what happened in their divorce, things like that, people want details. So if a guy is like, “No, we just didn’t work out,” and they’re kind of vague about it like that, I mean, where is it a red flag, and where is it like, okay, that’s just who they are, and you either can like them or not?

Celeste: Well, if they could potentially be married, is that what you’re saying? Like, “I’m a little vague, I’m divorced,” like—

Jessica: No, I didn’t even—

T.H.: Like, yes.

Jessica: It’s so funny because that’s so not where my brain goes, because I’m such a person who walks around believing what people tell me. No, but I’ve been on dates with guys before, and they’re just not very open about whatever made their marriage fall apart, whether it was infidelity, whether it was—I mean, even if they grew apart, I feel like there are ways to explain it. I’m just thinking of one person in particular who was very vague, and I felt like it was a long time, and I never really found out even what happened. For me, I feel like—but then some people are like, “I don’t want to know the details.” So it’s like—

Celeste: What date? What date was this when you were asking all the details?

Jessica: I don’t remember.

Celeste: Like, in the very beginning?

Jessica: It probably started within the first three, but continued on. I mean, even on the 10th date, I still felt like I wasn’t really getting information.

Celeste: Hmm, okay. Yeah, so that could be a couple of things. I mean, I don’t recommend talking about any type of ex, anything on the first three dates at all.

Jessica: Oh, okay.

T.H.: Wow.

Jessica: You tell men that too?

T.H.: That’s hard.

Jessica: That is hard.

T.H.: I want to know—

Celeste: But you’re getting to know the person and this—

T.H.: And then they might lie anyway.

Celeste: Well, you know what? I mean, at the end of the day, if they lie, at some time, you’re going to find out. But you want to get to know them as a person. Forget about all of their past. Forget about everything that’s made them who they are. The one thing you want to do is for you and that person to see if there’s chemistry, to see if you like each other as a human being, to see if he reacts to the waiter. Okay, right, the third date should be a dinner date. The first date, does he talk to people rudely? I mean, you find out so many things about that person. Mind you, you haven’t said anything about children, exes, past relationships, what went wrong. Because when you jump into something [like] that, that can really stigmatize someone. That can really like, “Oh, my God, that…” They’re thinking of you from things that were in your past, or things that don’t define you. I think it’s really easy to judge and define someone because of a past situation versus “Let me get to know you, T.H. before I start asking some deep questions.” That person that tenth date, Jessica, if he’s still not telling you, it could be he has trust issues. He has a lot of other things going on that you don’t want to deal with. That’s also kind of is a red flag, right? You don’t want someone that maybe is very new into this and you’re just not at the same level in the dating world.

Jessica: Fair.

T.H.: I feel like when I was dating, I wanted to just get my story out of the way. Like, “This is what happened. It’s over. Okay, now can we like start talking?” I almost didn’t want it to linger. Let’s just get it over with. Let’s get the ugly over with. Okay, let’s go play ping pong. I did, I was like, “All right, what’s your shit? What’s my shit? Okay, and so, what did you do today?” That was kind of what I did. I feel like I got to know people when I was texting with them and talking to them before I got to meet them in person. I don’t know—that was kind of getting to know them as a person. It happened more during the texting initial meeting time. Then when we met in person, I was like, “Bleurgh, here it is. Okay, now what’s next?” I will say that it is very telling to watch who you’re going out on a date with. The man who I’m with now, from when we ran into each other, we were together every day after. But the third day after, we go into a restaurant that he goes to often, and he’s saying hi to the maître d’, he’s shaking hands with the busboy. He’s talking to everybody who works there and treating them as if they’re his best friend, just with total respect and such a nice—I was like, “Oh, my god.” I really liked that. I never was looking for that, but I saw it. And that totally resonated with me. Another guy I went out on a date with, not only did he not pick me up, did he not meet me at the door, he was already seated at the table. It’s because he’s super short and he lied on his profile. When he got up, he was wearing high heel motorcycle boots, and he was still super short. But all of that turned me off. Maybe him being short wouldn’t have turned me off so much if he hadn’t done all of that for his own issues. My man is short, who I’m with now. My dating filter was like, “You have to be over 5’11”, whatever. Frank didn’t fit any of my filters, except he’s divorced and has kids. All the stuff about going to the gym or whatever, he doesn’t fit any of that. But I felt like this other guy had such—he felt sensitive about his height, that he was literally hiding in the corner in the booth at a table already when I walked in. That just left a bad impression on me. If he hadn’t done that, maybe I would have liked him a little more. But I was like, “Ah, I don’t know, he’s already got issues. I can’t deal with any more issues.”

Celeste: Well, starting out with a lie like that, I always tell my clients don’t ever lie about your age. Don’t lie about your height. Put current photos within a year timeframe.

T.H.: Yes.

Celeste: Because we’re going to find out that just as ugly or you’re going to turn us off. No matter if it’s not a big deal if it’s an inch or two, or I don’t know, I’m just saying that is so huge, because that sets the tone of the relationship.

T.H.: Yeah. 

Jessica: Yeah.

Celeste: And so no wonder you’re turned off. It’s happened to me as well. 

T.H.: Yeah. We should do another podcast about all the things we liked and didn’t like in the dates we’ve been on.

Jessica: And all the lies. I was surprised, like in conversations we’ve had and in real life, it definitely seems when it comes to lying on dating apps, that women are more inclined to be fake with their pictures, either their pictures are so filtered, or they’re using pictures from a while ago, before they’ve gained 20 lb or whatever it is. But that I was surprised that men are more inclined to lie about their age. I would have thought that women would be doing that. But I actually did meet several guys online who turned out had lied about their age. I just was like, that’s so lame.

T.H.: Wait, but they probably knew that you wouldn’t have found them otherwise, because they would have—

Jessica: That’s exactly why. That’s exactly why, because they’re trying to fit into a certain filter. But I’m like, but I’m your age, and my age is on there. I just feel like it’s just really lame. Like you said, Celeste, to start off on the foot where you’re already lying, even if it’s a little white lie and it’s somewhat harmless, it’s more like it’s just who you are. It’s indicative of your character I feel.

T.H.: Well, and also insecurity, lack of self confidence. Like, you’re not there. You’re not wherever you’re supposed to be yet.

Jessica: Yeah, well, there’s much more to continue on and discuss. We’re definitely going to have to get back to more of it. But Celeste, thank you for giving us a peek, a sneak peek at the inside of what guys are thinking and what you’re training them to do.

T.H.: And what women should look out for.

Jessica: That’s right. That’s right. For everyone else out there listening, we hope you enjoyed this episode of the Divorce etc… podcast with the exEXPERTS today. If you have, please help a girl out. When you subscribe, rate, and review, it helps us get the word out more so we can help support people like you going through divorce and beyond. Check the show notes for more info on Celeste and her Down and Dirty podcast. And of course, share this episode with anyone you know who can benefit from listening. Have a great day.

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