How to Do It

Women Keep Interrogating Me on Dates—and They Don’t Like What They Find

Some of the women are actually offended.

Man looking dejected off into the distance while his head rests in his hand.
Photo illustration by Slate. Photo by PeopleImages/iStock/Getty Images Plus.

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Dear How to Do It,

On Match.com, initial dates are often like job interviews where potential partners ask questions and judge the other on these questions, as well as appearance, body language, and so forth. I would seem to be a real catch. However, that is until the woman I am dating asks if I was married.

If so, how long? And if I have kids? I explained that I have been divorced for 10 years and that my adult son, age 20 lives with me until he becomes independent. The woman becomes curious and over the next number of dates begins to probe further and further into my divorce. I try to give as few details as I can and I’m usually vague. However, the woman I am dating quickly picks up that I had a very challenging divorce and custody battle where I won almost full custody due to my ex’s instability.

In fact, my ex came out quite badly in the divorce as she acted out in court. What seems to happen is that the women I date are uncomfortable with the fact they garner and are put off or put out. Some of these women are actually offended and believe what happened wasn’t fair to the mom. Some might want to meet my ex. It feels like I am in an intense job interview where red flags appear in conversations with employers. How can I get around this obstacle? I say that my ex and I have peaceful exchanges and have had these peaceful exchanges for a number of years. Am I fated to short-term, intense relationships through something like adultfriendfinder.com until both my kids are grown and out on their own? I would be grateful for any answer that either of you could provide.

Rich: I wonder if we are being given the exact nature of these red flags. The writer says that they keep things vague, but obviously, the conversations go on beyond that.

Stoya: I think the biggest red flag is his approach. I mostly advocate laying your cards on the table for efficiency purposes, and that does apply here. But imagine if I went on dates and I was like, “Oh yeah, I used to make suggestive artwork.” And then on the third date, I’m like, “Well, it was very sexual.” And then over the course of several weeks, I arrive at, “I used to be an adult performer.” That would be very strange. It would cause the person to question what I’m hiding and what they might find out next.

I think one thing he can try is saying, “Nice to meet you. I had a really nasty custody battle with my ex. We’re totally civil now. I actually prefer not to rehash the details over and over. Tell me about yourself.”

Rich: Also, I think given the way things usually go—and I’m not an expert in family law—it’s pretty drastic when the mother loses custody entirely. I mean, that usually bespeaks an intense situation, at least as it’s been presented to the court. The court, generally speaking from what I understand in these situations, likes to keep mothers with their children. That’s our cultural default. And so that’s what’s kind of tripping me up, that that is self-evident to me. I hear that story. The father has full custody of the child. And I think, oh, wow, something really must have gone down. And yet somehow in this retelling, multiple women are saying, “Oh, that doesn’t sound fair.” So what was unfair? Did he have more legal muscle? Was he somehow more aggressive legally? Or are they just defaulting to a stock narrative about patriarchy?

I don’t know. I feel like we’re missing something. I feel like there’s some component of this that maybe doesn’t strike him as being important that multiple people are picking up on and being like, wait a minute. So obviously I wouldn’t want to put him through the same rigors that he’s going through with his dates and a letter is only so long compared to extended, multiple conversations with people. But I feel like I can’t exactly judge the situation without knowing a little bit more. And I’m just inclined to say if a bunch of women, especially if they have no communication with each other are being like, “Eh, I don’t know about this one,” I’m more inclined to listen to that consensus and be like, OK, maybe there’s something there.

Stoya: I think that’s a really good angle and I’m glad that you see it that way. Because my take was all about presentation.

Rich: I think that’s a great point too. And I kind of missed that. It could absolutely be one of these two things. I mean, it would be irresponsible to completely ignore the fact that something might be striking people somehow as off. Has this guy talked to other women who are close to him in his life? Does he have a sister? Does he have other relatives? Does he have women friends who could give him a proper kind of assessment as to how they see it or how maybe other women might see this situation? You know?

Stoya: Yeah. And I think also he could think back on what all of these women have said. What wasn’t fair? Why are they offended? That’s useful information that he can use as well.

Rich: Yeah. When he talks about his ex-wife, how did he put it? “Oh, her instability. She came out quite badly, acted out in the court.” What kind of language is he using to describe this? Is he denigrating her in the process? I mean, it is one thing to have a cordial relationship with somebody that you made a child with. It’s another thing to describe that person—who knows what he’s saying? So I don’t know. This could be a case of him showing these women who he is and they are completely and justifiably put off. I just feel like when there’s that pattern of people, of disconnected people, you have to kind of wonder what the common denominator is. You don’t have to wonder actually. It’s you. So what is that?

Stoya: I keep going back to this sentence, “How can I get around this obstacle?”

Rich: Yes.

Stoya: And that one feels sort of strange for me. There’s no getting around it in the short term. In the short term, our writer could not mention his children. Not mention the whole thing. But after a couple of months, the children are going to become apparent, or child.

Rich: Children. But the child, adult son.

Stoya: Yeah. So eventually the children will become apparent and then that will be an enormous red flag. That’ll be a red swimming pool cover, Olympic-sized.

Rich: Yeah. I think that I would look at my language first. So what is it? What are the details? What is having people jump off? And the other thing is, yeah, dating can feel like job interviews. That’s just kind of the way it goes. Especially when you get older, because these women that he is meeting with are probably sick of putting up with shit: “Let’s hash it all out before I commit to you emotionally.” That’s just going to be the process. You might as well make it as fun and as enjoyable as possible by learning how to be a good conversationalist.

Now, it could be another thing too, if he’s somehow, I don’t know, targeting a demographic that is looking for something in a man that he can’t provide, even if it’s superficial. Say he’s meeting a lot of superficial women who quickly learn, oh, the money that I want to extract from you, I will not be able to because of your obligations with your children, whatever. You know what I mean? There’s so many different potential variables, but still all of that is coming from him. So he either needs to kind of use his words better, understand what he did, cast a wider net, or sift through a different crowd. We don’t know anything about the women that he’s choosing to meet with and what they’re looking for.

Stoya: Yeah. So, sorry. Not enough data.

Rich: Not enough data.

It happens. But I need to know what you’re talking about. I can’t properly assess. You got to give me the details. I know you got to be pithy and you want to be published in this column, so you can’t write pages and pages and pages. I know. But sometimes people are very selective with their details and it puts us at a disadvantage.

Stoya: Well, it puts everyone at a disadvantage, doesn’t it?

Rich: Yeah, it does.

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