Prepping for First Dates After Divorce with Susan Winter | S2, Ep. 17


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 T.H. & Jessica. 

Jessica: Today we’re so excited to welcome back Susan Winter, relationship expert, who knows everything that you need to know about dating in the post-divorce realm. Today we’re going to be talking about first dates, of which there is so much to know. So many tips, so much protocol, so many questions that we have. Susan, welcome back. Thank you so much for being here.

Susan: Thanks, Jessica. It’s a joy. I really love our conversations. This is like two girls talking on the phone just chatting away.

Jessica: And that’s exactly what it should be.

Susan: I know.

Jessica: For everyone listening, we hope you guys enjoy it as much as we do. We’re going to jump right in. I mean, when it comes to first dates after divorce, you’re finally getting back into the swing of things. What’s the most important thing to think about?

Susan: Well, let’s talk about the selection process. Let’s back up one step. The selection process is you clearly know what you don’t want, that’s why you’re divorced, right?

Jessica: That’s true.

Susan: That’s a clear indicator of what you do want, so it’s the opposite. If I want somebody to pay attention to me, and I want them to be kind of nice, and involved in my life, and value me and what I say, and what I think, that’s the target group that you would be looking for, whether you’re meeting them through setup dates, a matchmaker, in real life, or online. You go in intentionally thinking about who you are today and trying to match a prospective mate that would resonate with who you are, what you’ve learned over the course of the last 10,15, 20 years. So that’s one.

Then number two is the whole dating. Like, how do you date? What happens on a date? Who pays for a date? What’s the protocol? What if they want to kiss you? And do you have to kiss as well?

Jessica: Yeah, I want to get into all that, but I want to back up to what you were talking about for the selection process. What do you think is the biggest mistake you see people making when it comes to the selection process because that’s crucial?

Susan: It is good. Sometimes they go on an old prototype. You need to update who you are today, and it’s to your benefit to filter in who you know that you’ve become throughout the process of your marriage and as you’ve transformed into the woman that you are today or the man that you are today.

We need to think in terms of not what you would have chosen years ago. Maybe what you would have chosen would be a frat boy or a sorority girl, or a certain looking good person and you married that. It didn’t look that good. It looked great on the outside, and it was empty on the inside. We need to factor in a little bit of your growth. That’s where you’re seeking the things you didn’t get in your relationship. Now that you’ve discovered how you’ve grown throughout your former marriage, you need to go back to the drawing board. I would really urge you to go for qualities that you want to see in a partner. So many people do the external list like the guy has to be this tall, she has to be this young, they start doing the list, list, list. I promise you you’re never going to partner with somebody you find pug ugly and repulsive. It’s never going to happen, so we don’t have to worry about mentioning that. I need somebody who has a lot of integrity because my former partner lied all the time. I need somebody that I can trust and feel comfortable to be myself because I didn’t last time. I felt like I was walking on eggshells. And so those are important. You start to put those as the dominant traits that you’re looking for in a prospective mate. That’s how we’re going to do it differently. Then allow yourself some latitude for how they’re going to show up. They may show up in a slightly different package, like oh, no, no, I don’t date guys that have a motorcycle. Oh, no, I don’t date somebody that’s a teacher. No, no, the financial service dudes never dating one of those. We have to –

Jessica: It’s really breaking out of those patterns, so to speak, that you’ve been in before, right? It sounds like that’s what you’re saying. Okay, I feel like honestly, we could probably do a whole interview just on the selection process. That would actually be a really good interview about all of those things, because in online dating as you know, I mean, look, you’re relegated to a kind of starting off the choice based on the pictures, and it’s so superficial and shallow. A lot of people don’t know how to be open-minded. I’d love to hear your perspective on that. We can do a whole interview on that, but let’s move forward into the first date. You’ve made a selection, [Yep] okay, where are we going from here?

Susan: If you met them online, and you can, again, this is being recorded during COVID, you want to meet them in real life as soon as possible because you want to see are they really 5’2″ or are they 5’10″. You want to see do they look anything like their photos and are we going to get along?

Many people make the mistake of having protracted ongoing chats, text messages, or conversations and they start to like this person. Then when they meet in real life, there is no chemistry. Now that’s really cumbersome. The goal is to take it from however you met to in real life ASAP. Two, I still prefer a proper date. I’m guessing we’re not talking to a lot of 20-year-olds, but this thing about hanging out, and you’re hanging out and what are you doing? They don’t date. They somehow end up in bed and then talk a little bit later. Listen, I deal with this all day long. I’m thinking there’s a more effective way to do it, but I actually like a proper date, and I think to start small. You may have somebody ask you to dinner or you may be inclined to, let me do this right. I haven’t dated in a while. I’m going to ask her to dinner. What you really want to do is just dial it back a little bit. Let me meet for coffee or an early evening drink, that’s acceptable, nothing late at night. You don’t want to get involved in that if you have a little too much to drink, you’re not thinking right. Just a cup of coffee, in and out, it’s just a feeler. The first time is just, how do I feel, how does it look, and you’re kind of getting some basic information. That’s one. It’s not a high-stakes event.

Jessica: I have a quick question. I have friends who will go out and they will meet a guy for a drink. We need to talk at some point about an exit strategy, but they go out for a drink, and then they’re thinking to themselves if it goes well then it’s going to extend into dinner. Do you think that’s a fair expectation to have or not on a first date?

Susan: It can happen, but I wouldn’t. I would make it a compartmentalized thing so you get in and get out. So that when you are asked say, I would love to, but listen, if you really feel like doing this again, I didn’t have it planned, but yes, I’m going to go home and eat. I would compartmentalize it. It’s less pressure for you, you’re new to dating, and you want to get a feel for the person. Maybe you want to go home and think about it. You seemed so charming. There it almost scared me that might be too good to be true. You want to see if they’re going to call you back.

Jessica: That’s true. That’s true. Okay. Okay. All right, so continue?

Susan: That’s a good question. Let’s say you had a first date. That is just for your gut feeling, do I feel safe? Do I feel good? Now it’s worth it, your senses are recording at all times. Our mind is recording everything. This is why when they take people back into hypnosis they can solve cases from like 70 years ago. They find the last remaining person that remembers seeing a kid pass the school bus or something. You will have gotten a lot of data and that is the only point of the first thing is to just take some time and go through that data. If nothing, you’re not getting any huge red flags, you’re not feeling uncomfortable, it feels good, indicate. This is independent of male, female, straight, gay. Indicate your interest. Even though you might be shy and uncomfortable for being vulnerable, showing them you liked it, just let them –

Jessica: What’s the best way to do that?

Susan: I had a really good time. You’re a fun person. I actually kind of hate this dating stuff. I’m new to it, but you made it fun. I’d love to see you again. And then you leave it up to them. If they’re going to call you, they call you. I guess I’m speaking from a woman’s point of view.

Jessica: Sure. I think it’s fair to say that more women are listening to us than men. But then there comes the whole question like, I have a friend who thinks if they don’t ask you out on the second date, on the first date, she’s out. She’s like they have to ask before you leave, and if they don’t, if they text four days later, she’s already like, no, forget it. They’ve lost the window. I think she happens to [inaudible] her dating rules.

Susan: Those are some very harsh rules and somebody is lecturing her. You have to understand for everyone that you meet, they have been lectured by somebody. If it’s a guy, he has been told by guys that didn’t update this since junior high school. Oh, you know what? Act cool. Act cool. I actually had a guy – [Wait three days!] Yeah, yeah. I had a player, so I dated players for six years. I’m a relationship girl and never even did a one-night stand. I mean, this was horrible for me, but what am I going to say? Oh, I’ve had decades-long relationships, follow my relationship advice. Nobody wants that. I can’t talk to them about what their issues are. The one guy, this real hardcore player, said, okay, I know I’m breaking the two-day rule, but I had to tell you how much I enjoyed seeing you and I want to see you again. I’m like, what’s the two-day rule? [Laughs] This was a long time ago. I have met so many guys that they really like a girl at the end of the date and they’re so nervous. They just got through that and they didn’t screw anything up. They’re like, just sometimes when a guy doesn’t – [Get out while you’re ahead] I had a boyfriend, I said, why are you so quiet? He goes, I’ve learned the less I say, the less I can screw up. I have a better chance, right?

Jessica: That’s so true.

Jessica: Why is it that girls think that too? You’re like, again, stop while you’re ahead. You don’t want to end up trying too hard, putting your foot in your mouth at the end.

Susan:  Right. Understand that if you’re a female, and you’re wondering why he hasn’t called you back, he may be getting advice from his guys that say, dude, don’t call her for another three days. She’s a really good-looking woman. She’s got a lot of guys after her. You have to play it cool. Fortunately, I know so many people know my work that inevitably I will get a call at least once every couple of months. Somebody goes, Susan, listen, my friend’s asking me this. This is what you said. Wouldn’t you say this is true? He likes this girl, he wants to ask her out, and everybody’s telling him to wait a week. I’m like, no, no, no, no, ask her out right away. Because if you can get up the courage fellas, to ask out a woman right away, or ladies, to ask the lady that you’re dating right away, just don’t let it go too long because we do lose interest. We start to think, oh god, another person’s going to ghost us, so we don’t want to go through that. There’s an apex of interest and that starts to decline as time passes. If you like somebody, give them some kind of notification that you’d like to see them again, and see if they’re amenable to that. That’s it.

Jessica: What’s your take on, because I totally agree with you of getting them off the app, try to meet in person as soon as you can, what’s your take on phone conversations before meeting in person or Zoom or FaceTime calls before meeting them in person? How do you feel about that kind of stuff?

Susan: That’s fine. I think the more you know about them, the better. I think it’s important to go from chat to phone call. You have to remember a lot of young people don’t even have voicemail such situations set up. They don’t even use this thing.

Jessica: They don’t use phones at all.

Susan: No, it’s a camera. It’s not a phone. If that’s your comfort level that helps you then that could maybe save you a drive across town for an hour. Like, I’m not sure this person is kind of – If you question at all, like it’s Friday, it’s raining, I don’t know. Let me get this person on Zoom, and you see you’re not really that excited, and then you saved yourself time. That’s okay.

Jessica: How do you, because I’ve been in this situation myself, and I know a few other friends have too, you have these great phone conversations with a guy a couple of times before you’re supposed to meet in person. Inevitably, you get your hopes up, and you have all these high expectations. It’s almost like you’re setting yourself up for disappointment, because to what you had mentioned before, you might have this great chemistry or banter on the phone, and then you meet them in person and you’re like, womp womp.

Susan: I know.

Jessica: How do you keep control and not get caught up in things?

Susan: Well, you can’t, and you don’t know until you get there. That’s the thing because you can have nice friendship and banter, and then if you see somebody that is definitely off your radar, definitely friend zone, and it doesn’t work. I’ve had guys that were so – they didn’t want to pay for a date. I’d show up and they’d look at me. They offered drinks and then they’ll go like, oh, you’re good looking. I’ll take you to dinner. I was like what, I earned a dinner? It’s like they see me in person they think I deserve to –

Jessica: You look so much better than your pictures.

Susan: You’re agreeable for me to have dinner with. Yeah, that does happen sometimes. Listen, there’s no such thing as perfect. You may over-talk to somebody because you can’t physically meet and then be disappointed. You can under-talk, meet them, and they’re wonderful. Just as a rule of thumb, don’t get stuck chatting on an app until you have a physical visual of them because they may not be who they are. Their photo may look totally different. What you think is gorgeous in the photo may not be what you know to be [accurately represented]. I’ve written enough guys’ profiles to know that they’re not witty. I am. So many of you are dating Susan, you just don’t know it.

Jessica: Oh my god. That’s hilarious. That’s a service, girls, and guys out there, that you can get when you find Susan afterward. What are some other really important first date protocols or tips that people should be thinking about that they might not be considering?

Susan: I think we tend not to think about this. We tend to get a little tension around it, the sexual pace. I really want to address this [yes]. On first dates, I don’t care what time period it is, you are not required to do anything. Guys oftentimes feel they have to go in for the kiss or it was ineffective. Women sometimes feel like they need to make them feel good by acting interested. Just throw all that garbage out. Be true to yourself. Don’t let anyone, anyone, anyone push you faster than you are ready to go. Don’t let them push you into a physical anything if you don’t feel like doing it. It takes time. Some of us are immediate, others, it takes a long time. I’m, the last thing I do is the bedroom. Yeah, so I’m a long time, and it could really throw people off. I understand that. I can articulate that but just go at your own pace. Don’t beat yourself up if you intend to go out with somebody, they were drop-dead gorgeous, you’re like, oh my god, and they’re charismatic, and you just end up doing the walk of shame at 7 am pretending you always –

Jessica: I think that’s a big challenge though for some women, especially coming out of relationships where it may have been for a long time, it may have been for an extended period of time, but they were so unhappy. They feel like they haven’t had any kind of emotional or physical connection in such a long time. Then they go out and they’re kind of like, but I don’t want to be a slut.

Susan: Men are okay with it actually. I mean it’s just a different –

Jessica: Well, wait, do you think that the old rule doesn’t apply anymore? Like, if you do too much, and then he thinks you’re trampy and then he won’t call you again? Do you think that that’s out the window? You don’t think there are guys out there who think I’m not going to take her home to my mother?

Susan: Frighteningly, men have a double standard. I know because I hear from many of the coaches that are coaching men right now. I hear from therapists that can’t go to another therapist because they don’t trust them. I hear a lot of stories like, I’ve had very modern young millennial guys tell me and express an interest in a woman knowing that she has a lot more sexuality under her belt, a lot more partners, and was jumping all over them on the first date and kind of I like her, but I want her to be my girlfriend. They’re ashamed to say I have an innate prejudice that she should be pure.

Jessica: That’s so interesting that what you’re saying right now is that there are young guys out there who feel ashamed if they actually have sex, or fool around a lot with a woman on a first date because they feel like she shouldn’t be doing that.

Susan: They get disappointed in her. It’s their modern, that’s not politically correct I know, that kind of –

Jessica: Yeah, but if that’s the reality, everybody needs to know that. That’s why we’re here today.

Susan: It did shock me and this is why I love it that men speak to me so honestly. Ladies, be aware that men no matter how modern they are still carry an innate double standard. It is really age-old, but they want their woman to be a bit of a prize, and they don’t want to get you so quickly. Here’s the deal. You think it’s never going to happen, you couldn’t care less, sleep with them right away because they’re disposable. It doesn’t matter. With guys like that that I knew, I look at them and was like there’s like no way this is going anywhere. I remember saying six days later, so you ever going home? No offense, I like you, but you haven’t gone home since Saturday night. We’re having so much fun. But there are guys for that. Men do this too. But in the beginning, you’re going to be touching, tasting, smelling, looking at, and reevaluating everything. Just try not to beat yourself up. You’re going to have some dates where you fail spectacularly. You’re like god, he was such a good guy. I can’t believe I said this, or I did that, or I tried to look cool. I lost him. Believe me, there’s nothing you lost that was really yours. You can be so abusive, and so out of alignment with guys that are going to be your guy and they just kind of hang in there. It’s okay. You’re going to make mistakes, you’re going to be marvelous at the same time, so cut yourself a break. When you sleep with them and how you sleep with them, the reason that as women we try to slow this down is we want to get a bearing on who he is and how safe are we with him emotionally. [That’s right] Even if you decide it’s going to be for fun, is he a guy you can talk to the next day, or is he suddenly radio silent like, I got what I wanted. Goodbye. You’d like everybody to treat you with a sense of respect regardless of what the romantic design is.

Jessica: I also think that there are, I know from firsthand from conversations with friends of mine, there are some women who can be sexually satisfied with a guy they really don’t know all that well and met that night and they can sleep with them. Then a lot of women who are like, it’ll never happen for me because I don’t have enough of a connection with them. Regardless of how hot they think the guy is, or how hot the guy thinks the woman is, it’s just not going to be satisfactory in the end.

Susan: Dating is learning about yourself. You may learn this time around that you’ve got different component parts that you didn’t have before, you didn’t recognize them before, or you didn’t need to know them before, because you walked into an established design of a marriage or a living together relationship. It had a certain protocol and it had certain rules. Now, you are out testing everything again as you are looking at the entire buffet table of what is available and designing who you are today and how you participate. That’s the interesting factor. You’re going to again, please allow yourself latitude. It’s never a mistake if you’ve never done it before. You’re going to be going out and gaining information. You can start down a path and then just go, oh my gosh, this is horrible. What did I do? You just didn’t know. You have to go through this process, right?

Jessica: I think it’s so great for everyone listening to be feeling they’re getting permission, that may not be the right word, but getting permission to, like you said, grow, learn who you are, go with the flow. Maybe you’ll make some mistakes, maybe they’re not really mistakes, they’re just learning, and it’s part of the learning process. I think that’s really great. Are there any other specific things to specific do’s or don’ts when it comes to first dates in particular?

Susan: I am of a generation where men paid. I understand that this is a dicey area depending upon your age. I think on the first date if you’re having coffee, and he doesn’t pay, I mean, what are we talking about? Worst case scenario, $4? It’s the first date. I still think that until you’re an established couple, you don’t start splitting that. I think it is the duty of a man to court, but you will notice there are men who don’t pursue anymore and it’s partially societal and it’s a lot to do with the male coaches on YouTube. I get their refugees that are like, I don’t know why women aren’t happening for me. I’m like, you’re not pursuing them. They’ve kind of been emasculated and told to not pursue women, and so this is getting to be a problem for some of them. Don’t assume that your guy is being disrespectful. He might be disrespectful, he may have no clue. The important thing is that you need to know how you want to be treated. You need to know how you want to be dated. There is nothing wrong with stating that either in your profile or having a very delicate, brief, and direct conversation with a man. You could even have it kind of a third-party conversation like a philosophical thing. You know, it’s funny, a lot of guys nowadays, they kind of poo-poo courting and dating. If they only knew how much it means to a woman. I mean, it feels fabulous. You can kind of say it that way. [I love that] I always jumped to the philosophical. I don’t want to go directly. I will recall something in the past or give an observation. I have a lot of girlfriends that find themselves going on dates and splitting the bill. I understand if you’re both living on ramen noodles as undergrads, I understand that but it’s hard when of a certain age and the guy drives up in a Mercedes and he won’t buy you a drink.

Jessica: Well, it’s funny, I was out on a date fairly recently with a man. He did pick up the bill at the end, but I generally, my rule of thumb even on a first date, is I make the gesture. I reach for my purse, I try to pull out my wallet, and he was like, no, I’m paying for this. Then he turns to me and he says, you know, you should never be paying for dinner on the first date. The man should always be paying. I don’t remember how exactly he said it. I said something to the effect of, I totally agree with you. I’m always going to offer, but if he accepts, I’m never going out with him again.  But I do feel like in today’s day and age, it’s important to make the gesture. I will actually, I mean, listen if I pay I pay, but it is true. I feel like I also at 48, I also have the mindset that I think the man should pay and not just the first date, but to appease society, I do offer.

Susan: Then second and third dates, you may feel close enough to this person that by the third date, you want to order something for them, or go to a restaurant where you’ve got something set up, or cook them a meal if you feel comfortable letting them in your house. I mean, there’s more than enough time to do that and be that generous person. But in the beginning, in a heterosexual relationship, I think at least that’s the kind that I know, I appreciate a man showing his appreciation for me by doing that. That’s why I start with coffee, like coffee or a drink. It’s not a big expenditure. I don’t want you to have to spend $150 or $200, and I’m never going to see you again. That can be very, very expensive. We do it a little bit differently now to allow everybody a date.

Jessica: Yep. Okay, any last-minute specific do’s or don’ts that we need to know?

Susan: Listen to yourself. You’re going to have a lot of people in your head. Most of your girlfriends and guys, the same is true, most of your guy friends, they might try to dampen your excitement over somebody like, you don’t know, you don’t know, don’t get hurt. [Totally] I have images of these [whooshing sounds] big birds, just hovering over us and trying to protect us. It’s like you have to crawl up to the edge of the limb. Sometimes you just have to go, and it might just work out. So, listen, take your own counsel, trust yourself, trust your gut, and learn to trust yourself. Listen to what your friends are saying. If they’re all saying the same thing about the same person, do listen up. But for the most part, use your own intuition and find your own red flags. Remember you have your own reasons. You know exactly why you’re dating, you know what you’re looking for, and so follow your instincts and trust yourself.

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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