If they ask about my dating and sex life, are they interested?

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I keep seeing variations of this question, and similar questions show up in all corners of my life:

Why would they ask who I’m currently dating?

Why would they ask about who I’ve dated in the past?

Why would they ask about my sexual history?

What does it mean if they ask me how many people I’ve slept with?

Do you think that means that they’re interested?


The thing is, when someone asks you a question about your dating history, or your sexual history, it CAN mean that they’re interested in you in a romantic way. But, it doesn’t always mean that’s the case.

Here’s a great example: Odds are good that if you ask me for dating advice, I’m going to ask you about your dating history. If you ask me for sex advice, I’m probably going to ask about your sexual history. If I’m interested in you romantically, I would never ask you how many sexual partners you’ve slept with, but I might ask you when was the last time you had unprotected sex. When I ask people about their dating history, my motivation is usually information seeking rather than trying to get in their pants. But that’s just me. Some people ask about your history to figure out what sort of stuff you are or are not into, or they’re looking for information to use to shame you in some way, or they just want to get in your pants. There’s no real universal answer as to the motivations behind what people do. Oh and on the flip side, people talking about their own dating and sexual experiences doesn’t necessarily mean that they’re interested in you. I’m pretty much an open book when it comes to sex, dating, and relationship talk. That doesn’t mean I want to date and sleep with everyone I meet, I’m just a very open person about that sort of stuff. There are things I wont talk about with strangers, but sex, dating and relationships aren’t those things.

That said, yes, sometimes people ask about your dating and sexual history because they’re interested in you. There isn’t one real way to know for sure, but you can usually tell based on three things: First, tone. Second, the way in which the phrase things. Third, your existing relationship to that person.

The biggest clue for me will always be tone. Verbal tone obviously, because flirting sounds very different from say, a political discussion, but also the general tone of your conversation. If your conversation has a tone that is formal, it’s more likely that they’re just generally curious about your experience rather than trying to see if you’re the sort of person they want to share an experience with. This can be hard to read over text, but I feel like if you’re texting about sex and dating history, it’s a good bet that they’re interested because they’re interested in you. I’m using tone generally here to mean the overall vibe of the conversation. You know how you can just sort of tell that someone is flirting with you, regardless of the words they’re saying? Basically that. If you find flirty behavior hard to read, here’s a good way to tell: Does this person seem genuinely engaged and keeps pushing the conversation along? Some people are bad at sending non-verbal flirting cues, but I’ve always found that even people who suck on non-verbal flirting are still good at showing interest by being engaged. Whether in person or not, is this person continuing to open up conversation and conversation threads? It’s not always foolproof, some people are just talkative, but if they seem to be speaking to you in an informal tone, and want to keep the conversation going, AND they’re asking you about your dating and sex life, dollars to donuts, they’re asking because they’re interested romantically.

The way people ask questions can also tell you a lot. If I ask you something about your sexual history, in a fact based way like “Do you derive pleasure from oral stimulation?” it sounds less like flirting and more like a questionnaire.If I asked someone if they like it when someone goes down on them, or what they prefer in bed, it sends a very different message. The difference is going to come down to whether or not someone sounds like they’re asking a question that is fact-based and about prior experiences like “Are you sexually active?”, or if it sounds more informal, personal, and usually in a way that is a more focused on potential future experiences like “What turns you on?” or “Would you like it if…”.

Of course, some people just sound formal and clinical, or informal and flirty when they’re really not trying to be. That’s why your current relationship with a person matters for context. If you’ve already got a flirty rapport going, when they ask you about sex and dating, odds are good that they’re asking because they’re interested in you, and not just the answer. If they’re a relative stranger and they seem to have a general flirty tone, and ask questions in a way that seems flirty, probably a good idea to assume they’re interested in you. Again, not fool-proof on its own, but if you look at the tone the use, how they ask questions, and your current relationship, you can probably get a good idea if they’re asking because they’re interested or just interested in your answer.

Oh and besides all that,  my standard response to any question that is based on the premise of “What does it mean when someone does this?” the simplest way to find out is ask them. If you’re curious enough to ask me, take that curiosity and try to get an answer from the person who can give it to you.

Good Luck Out There.

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