Uncomfortable Post-Divorce Dating Questions with Susan Winter | S2, Ep. 16


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. 

T.H.: Welcome, Susan Winter. We love talking to our internationally recognized love coach and best-selling author. We feel like we get sneaky little tips from her.

Jessica: Totally.

T.H.: Today, we have a bunch of questions for her. They are how to ask the questions that you don’t want to ask when you’re dating, but also maybe how to answer those questions if you’re on the other side of it.

Jessica:  And to preface also how to ask the questions you don’t want to ask, but you have to.

T.H.: Oh, yeah. Well, you should.

Jessica: These are the conversations you have to have.

T.H.: You should.

Jessica: Right. Thank you for being with us Susan, so excited to talk to you about this.

Susan: Love you guys. I feel like we’re just in your living room chatting just like a bunch of girls. This is fabulous.

Jessica: That’s exactly what it should be.

Susan: The fact that we’re encouraging other women to have these conversations and to feel connected to this community is wonderful. It’s a great resource.

Jessica: It’s so important. The whole theme of this topic is really the awkward conversation. There’s no really great way to jump in, so let’s just jump in. We’re talking about things like asking people that you have met their status with having been tested for COVID, their status with having been tested for herpes, and all of the other battery of tests, the standard sexually transmitted infections questions.

All of the things that you don’t want to ask, but that you kind of have to ask if you’re going to start dating someone in order to be careful for yourself, right? You don’t want to be one of those people who doesn’t say something, and you’re not that careful, and the next thing you know, something happens that changes your life.

Susan: I know COVID is almost easier because it’s so — the death, the destruction, and everybody knows somebody who had somebody pass.

Jessica: Right. There’s no stigma these days I don’t think.

Susan: The way you may want to say it so that you don’t sound like a stick in the mud, but I mean, some people are very aware of the fact that they need to say something and they kind of feel embarrassed, not that they’re paranoid, but they’re concerned. They think maybe it looks like they’re uncool or that they’re rigid, and that when you’re first dating you’re giving somebody this ‘I’m uptight’ vibe, and you want to be comfortable and casual. In a case like that, I would pick realistically a family member or somebody that you need to see who has a compromised system and say, “Look, I have to ask this. I really want to date. I’d like to get to know you better. I have a mother that I visit twice a week and she is not doing well. I’ve had to be careful about my pod and my contacts. I do want to date. I just need to know where you stand on that and your level of exposure to other people. It’s not necessarily like we’re all out there at a party. It’s just what are you exposed to because I’ve got to protect somebody besides myself?” 

Susan: That’s actually a great idea. Pawn it off on someone else. Make it their fault. 

Susan: I kind of do it —

T.H.: Well, me being a little bit of a skeptic, do you ask for proof if they’ve been tested? Because you just met this person, and they could totally be lying to you because they just want to hook up with you or whatever they want out of it. They’d be like, oh yeah, no, no, it’s all good. It’s all good. Then maybe they’re not being honest. Do you have to push that question back? Okay, cool. When were you tested? Can I see those test results? Is that something –?

Jessica: Or if you’re making a date for the following week, are you saying, okay, we’re both going to get tested on Tuesday before we meet on Friday. Susan, what’s your opinion on that?

Susan: I never personally have known somebody, a client or a friend, to say, “Show me your test results.” I’m not saying that isn’t a smart idea, but most people I know just have the conversation and want to see the reaction of the person they’re with to see how intrusive is this. Meaning if they rail and like, oh, I don’t believe in that. That’s like I’m taking that as you take no precautions whatsoever. That’s already told me something about your disposition. I don’t think I would need to say show me your test results. I don’t personally feel that way, but every single individual has to make this decision for themselves, for their family members, for their own comfort level. I’m not diabetic, I don’t have a heart condition, but then again, we have people here who have this thing called Valley fever. I’m in the southwest in the wintertime, and it’s something from the spores that get kicked up. Now, a lot of people have ended up with horrible COVID. They’re quiet people, they do a small job, but if they had Valley fever that kicked off the COVID and flattened in 10 days in the hospital and is still trying to recover. We all have to be exceedingly careful. I personally would not need to see paperwork, but I would need to see the person’s disposition around my question.

Jessica: Well, that’s —

T.H.: So you read their body language.

Jessica: And there was someone that I went on a date with, and we had had this conversation. I think I had maybe just gotten tested. I think because I had ended up having Thanksgiving with T.H. and we were in a group that included her boyfriend’s dad and his wife etc. I did get tested, and I had my son get tested before we went. Anyway, I was having this conversation with this guy, and I think I was mentioning I had just gotten tested. We were having that conversation and what he told me Susan is very similar to what you just said. He wants to see people’s reactions to the conversation but based on their reactions, that’s how he determines if he does ask them to see their results. He said to me he did not feel compelled to have to ask me to see mine. I was like, “I’m happy to show them to you”, because I had them. But he was saying, “But that’s part of it. I can tell that you are being honest about the conversation and I don’t necessarily feel like I’d have to ask you to see them.” Or maybe his normal MO was he usually asks, but based on the conversation with me, he didn’t feel like he needed to.

But that’s an interesting thing because the problem is that you’re trying to use your intuition with a) a stranger b) someone that you’re not in the same room with so you’re only looking at whatever you can see from their reaction and their body language through a screen. I don’t know. Can you trust your gut with someone that’s literally a virtual stranger that you’re looking at on a screen? I don’t think it’s out of the realm of normalcy to say, “I like to see your results.” I mean, it’s not like they could be, “Why? You don’t trust me?” Like, no, I don’t fucking trust you. I just met you online. We’ve never even met!

Susan: Yeah, there’s such a wide variety. The same lady that I know that got very, very sick, she and I went out to dinner before I left Arizona last year to go back to New York. We were sitting outside in a socially distanced restaurant. I heard all this noise and drinking and laughing and they were under an outside tent area. They were like this. I’m like, really? I think the disposition of a person shows you how they live their lives and where their own boundaries lie. That tells you a lot about these difficult questions that you’re going to be asking. This man sounded like he had self-restraint and was thrilled with the fact that you did as well and that you were conscientious. That shows me you were —

Jessica: I don’t know if self-restraint is a characteristic I would add to my list for myself, but okay!

T.H.: Take the compliment. 

Jessica: That conversation then also still goes into, because I think that people also wonder, particularly COVID wise, you’re already apprehensive about how close are you going to get to someone.

Because dating and the patterns of dating are so different, and I don’t want to use the word expectations, but how quick someone is going to move with someone sexually, and how fast it’s going to take for someone to start hooking up together, brings into play this conversation about have you been tested for sexually transmitted diseases or infections, whatever it is that you want to call them, which is always a really awkward conversation to have. When do you have that conversation? Because do you have it so early on that you’re giving the other person time to go and get tested? If and when that time comes, you don’t want to wait until you’re already in bed like, oh wait, by the way… because then that’s not —

T.H.: Here you go! From under the mattress.

Jessica: Right. At what point is that an appropriate conversation? Because you also don’t want to bring it up too soon, and then you’re coming off like a total slut. Where does that fit in?

Susan: I think nowadays, this is hoping that they wait for at least one meeting or two meetings —

Jessica: Okay, we’ll give you two dates.

Susan: As you anticipate that you may be sleeping with this person, that would be the time to volunteer this information. “By the way, I have been tested. I’ve only had X amount of partners, and that was in this time period. Then I was tested, and I haven’t had a partner since then. You’d be the first person I’ve been with in a while due to COVID, so I know that I am STD-free or STI-free. But if you would prefer–” I think it’s a question that you have to have before you get involved in sleeping with each other. Because you also need to know, it’s the condom question too, like are you on the pill and the condoms and having children and where are we going with this? These are better discussed before you hit the sheets, not later.

T.H.: Would it be, I mean, I definitely don’t always practice what I preach, but let’s just say I do. You really like this guy, and everything’s going great. It’s always uncomfortable to have that conversation no matter what.

Jessica: The testing conversation or the “Will you wear a condom?” conversation?

Susan: Or the “Will you wear a condom?” —

T.H.: Or you can just pull out the condom and say whatever.

Susan: You know, here’s the thing, if they don’t have one with — I don’t know what’s up but European men just don’t want to use condoms. I don’t know, maybe American —

Jessica: I don’t think it’s just European men. [Laughs]

Susan: I’m sorry you can’t feel what you want to feel. I don’t want to die for you. I mean, honest to god, you know —

T.H.: [Laughs] And I don’t want to birth any more children.

Jessica: Right.

Susan: I think a lady should always have her own. If she’s actively dating, have condoms in your purse or by her nightstand. Not like she hands them out for candy but

just say, “I protect myself. I believe in having a condom. If this goes further, and we’re to be a couple, and we decide on exclusivity, then we can get jointly tested. If the trust is there, we can eliminate this or whatever.” Now, you ladies are still — you don’t want children —

Jessica: No, I sure don’t.

Susan: You’re on the pill or you’re not on the pill, because as far as having children, that discussion should be really early on. It should be in your profile. It should be in your first couple of dates what you’re looking for so that nobody is fooled. I mean, you don’t want to be dating a guy wanting children saying, “I’m 29. I’d really like to have children someday” and the guy goes, “Well, I had a vasectomy”. It’s something —

T.H.: You’re shit out of luck. Jess, tell Susan and everybody listening about herpes profile on the dating.

Jessica: I will say that I have seen, as I’ve been on some of the apps, that some men will write right in their profiles that they are herpes positive. One guy even wrote it to the point where he said something like you’ve got to give me a little credit for just putting it out there. I really have and that’s kind of how I felt. For me, I don’t think I’m interested, but I feel good for you that you are putting it out there, because you’re being upfront about it, and you’re not like beating around the bush. Frankly, that also has to be a very awkward conversation which was the next place that I wanted to go if you already have something. But I will also say that I have two women friends who have gone on dates with guys, I don’t think that the guys had necessarily written it into their profiles, but I know two women who have gone on dates with men, and the men have disclosed that they had herpes. These women did have sex with them with condoms, but knowingly, which again, to each their own. I guess it was nice to know, nice for the guys to know, or nice for anyone out there listening to know, that even if you have something, not everybody’s turned off by that. There are plenty of sexual partners to be had as long as you disclose it, as long as you’re honest in the very beginning. The scary thing is on the flip side of that. I also know someone who really had not had many sexual partners and was always super careful about having sex. Literally, one time dating in the last few months had sex with a guy, didn’t wear a condom, and now tested positive for herpes. She doesn’t know exactly — evidently, it can be dormant for years, so really the question is where — but it’s one of those things you have to just disclose where you’re coming from. These are conversations you have to have in the beginning. You have to have respect for people who have things that they have the balls to disclose because that’s got to be a really tough conversation.

T.H.: Yeah, embarrassing conversation.

Jessica: Right.

Susan: I had a colleague who used to sleep with stars, celebrities.

Jessica: Yeah, star fucker. We know those.

T.H.: Wait, what did you call them?

Jessica: Star fucker.

Susan: Well, a star fucker, right? And she, I won’t say which musician it was but very popular in the 80s, and she slept with him and got it from him. But herpes, [what a bummer] I look at everyone 50 and over and think you got herpes. I just start with you having —

Jessica: Why?

Susan: Because this was the no condom generation. The Woodstock generation didn’t use condoms. Remember women were on the pill?

Jessica: Wow.

Susan: This is when herpes had its prevalence — you know the herpes capital of the world is at The Villages. It’s enormous in northern Florida old people, like active senior citizens, environments.

Jessica: Who knew!

T.H.: I heard sexually transmitted infections have been on upswing [during pandemic] in assisted living centers and stuff like that.

Susan: Especially herpes. This generation had herpes.

I don’t know what it was, in California too, there is not one woman I’ve met with a man 48 or older, who doesn’t tell me then that she discovered that he had herpes three months in. “But don’t worry, I’ve lived with it for years.” So between California guys that are older, and older men, I look at you like I know you’ve got herpes. You prove to me you don’t. That’s just the way.

Jessica: Okay, so can we just say to everyone listening, listen to Susan, because you have to be so careful. You have to protect yourself. You have to make sure that you’re taking all of the necessary precautions for yourself so that you don’t end up in that situation. I have heard that just during the last year during the pandemic sexually transmitted infections have been on the rise. I think part of it is because I think people have been so much more focused on the COVID conversation and less focused on the wearing condoms and sexually transmitted infections conversation, and therefore have left themselves very vulnerable and open to getting other things. But it’s sort of shocking to me that the idea would be that the assumption is everyone over 50 has herpes. Oh my god, everybody needs to look at that and hear you, and really let that sink in, and think about it like that.

Protect yourself. It’s not that hard.

T.H.: And educate yourself. Talk to your doctor so that you understand what does that mean. What should I do? What should I not do? You have to be armed with information and really educate yourself. Don’t be a naive player here because you could potentially be the one getting hurt.

Jessica: Right.

Susan: It’s just that it isn’t necessarily you. It’s the people that are sleeping with the person that you’re with. Because remember the Woodstock generation, people now 65 and older, that’s why all these senior citizens homes are having a flurry of herpes, because that was the thing. Women were on the pill, so guys didn’t have to wear condoms. The condoms really came in the late 80s, because of AIDS. Now we’ve all started wearing them. Then when we all thought we were safe from diseases, the millennials started having hookups, the STDs went through the roof and keep multiplying. This is a very big deal. Now, there are a number of resources you can use. There are at-home tests, and there is a thing called ‘Let’s get Tested’. You can test for any one of these things at home, send it out, it’s private, nobody sees it, and then you get the results back, and they’re actually very good. There are even herpes-positive dating sites, because this girl who got herpes, then always had to have that discussion with every guy that she was with. [That’s right] She had long-term partners, and of course, it goes more into remission, but every once in a while she’d get a flare-up. She would have to tell them. She went on a herpes positive site, and then she said, oh god, they’re a bunch of horrible people there. I don’t want to be there, so she now lives in the villages [oh my gosh] where everybody else has got it, so she’s going to be fine, right?

Jessica: But you know it’s interesting that may have stemmed because that was sort of the generation because women were on the pill, but what I think is interesting, as we get to a certain age in our lives, that men who are in their, I would say maybe somewhere like mid-40s and above, who decided that they don’t want to have any more kids and now will go and get a vasectomy. Then they think that they don’t have to wear a condom anymore. You’re like, hello! It’s not just about getting pregnant. That is obviously a concern, but you still have to protect yourself from all of the other things. I just think that sometimes guys are really focused on am I going to get them pregnant or not, and not necessarily worried about the bigger risks.

T.H.: But a woman can do that too, like if you’ve had your tubes tied, and you know you’re not going to get pregnant.

Jessica: Yeah, but I don’t think that women are running out and getting their tubes tied as quickly and easily as men are getting vasectomies.

T.H.: It’s very easy to go do that, but it could go both ways in terms of being negligent.

Jessica: What were you going to say, Susan?

Susan: Well, I was wondering. You’re talking about vasectomies? Those were kind of rare. Are you seeing an increase?

Jessica: Yeah, I think so. Yeah, I think definitely.

Susan: I think it’s like, you know what, I paid out my first marriage. I’m not paying for another.

T.H.: Done. Done.

Jessica: And I think — [they don’t want kids]. Yeah, they don’t want kids and maybe are also at an age or whatever, and they’re like I don’t want to wear a condom, so here is the answer to my issues. I don’t have to wear a condom because I don’t have to worry about getting someone pregnant. They don’t have to worry then also what age range they’re dating in, because even if the women could get pregnant if they’re dating someone in their 30s or below, they don’t have to worry about it. I would say I definitely have spoken to a number of guys in that kind of mid-40s and above range that have had vasectomies or have talked about actively wanting to get vasectomies, and it has been surprising for me.

T.H.: There’s a guy I know whose kids are already in college and stuff, but he’s on a tear dating, and he just went last week.

Jessica: Yeah, they just don’t want to worry about it.

T.H.: He’s more worried about getting someone pregnant than anything else.

Jessica: And they don’t want to be 75 when their kid is 20.

T.H.: I mean, look at the celebrities.

Susan: Not only that, you’ve got financial implications because now you’ve got child support. They can date the 23-year-old girl and lose their mind, and now she can’t trap them with the baby.

T.H.: Right. You’ve already paid your child support. You already did your divorce agreement. This ain’t my kid.

Jessica: Right, totally. Oh my god. All right, girls —

T.H.: I love this.

Jessica: I know. There’s so much more.

Susan: I don’t want everybody to think that everybody over 50 has an STD.

T.H.: There are disclaimers all over this podcast.

Susan: Fortunately, I don’t date older men, so I will have to ask some different questions. But I look at my age group, and I know the way they lived, and I know that that was the thing for us. [Fair enough] Then I have to ask, were I to be so generous and so inclined to date a man my age, I would have to ask him that question.

Jessica: Yeah, it’s weird, but it has to be asked. The whole topic is so important. I think that it’s great that we were able to have fun with it here. We’ll have to continue doing that because it is an ongoing conversation for people to be able to actually get comfortable with it and understand that you can’t not bring it up.

T.H.: It’s your life. It’s your life.

Jessica: That’s right.

Susan: There’s another way to state it that isn’t so uncomfortable for you. I like to take things from the philosophical and you can throw them out there on the second or third date. “I know that people hook up. I know there’s a lot of sexuality that goes on now with COVID and everything else. I have decided that if I’m going to partner with somebody, and it looks like it’s going somewhere, I think the smartest thing is just to get it all taken care of. Show my results, it’s all cool, it’s all good, and then nobody has to worry about anything.” You can say it in passing like whatever.

T.H.: Right, that’s a great tip.

Jessica: That is great.

T.H.: It’s like a conversation piece.

Susan: And move on. Oh, how’s your bagel? Whatever.

Jessica: [Laughs]

T.H.: You want that toasted a little more?

Susan: How’s your virtual bagel? I don’t know.

Jessica: But no, you’re right. It’s all about trying to — you have to acknowledge the awkwardness of it or you have to work it into the conversation like it’s no big deal. Because when you make it into no big deal then it’s no big deal for them either. It’s like, listen, you’re expressing the fact that you respect yourself and your body enough to care and to have the conversation. That’s the important part.

Susan: Exactly.

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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