How To Ask A Guy About Past Relationships

April 6, 2021

I know from personal experience that asking men about their past relationships is a potentially awkward and even scary task.

A few years ago, I was just getting comfortable dating my first serious boyfriend and as a newbie, I was a little nervous about what to say.

Here is the kind of thing I said. “So, you’ve only been single for 6 months. That must mean you’ve had a lot of different partners.

What’s it been like dating all of them?”

He looked at me incredulously for a moment and then, while smiling in a non-threatening way, asked “Is that your attempt at ‘creepiness’?” he said, with the undercurrent of a little playfully annoyed.

I guess it was, at least in part. I said something to the effect that I really did care and wasn’t trying to be strange.

I’ve noticed that whenever someone asks me a personal question about myself, I am nervous, but as soon as they tell me something about themselves, they immediately relax.

I think psychology is pretty straightforward:

We stood cliff side looking out upon the infinite horizon of life.

I subconsciously see myself as a kind of personal assistant. I’m helping them out and therefore they will “help me” in return.

This is true whether I know that they are doing it or not. Even the most casual inquiry about a guy’s personal life makes them feel at ease.

In fact, I think this is especially true for men, because, well, why wouldn’t they?

Why would someone who is still in the single scene feel threatened by the thought of having another, less experienced person, poking around in the “men’s side of the market”?

I think that often there is a sense of shame and self-consciousness about being single.

Men don’t get the sense that they can “give out their number”, get to know someone new in a little bit of a cooler, more personal way, and if things go well, “move in together” (much less “get married”) with them and feel some sort of connection afterward.

That’s kind of a scary, awkward position for most guys to be in.

But from a woman’s perspective, this whole “one-night stand” thinking doesn’t really make sense, to begin with.

In some sense, it’s just a way to make sex and intimacy seem less scary, less forbidden

Paradise Found

I guess what I mean is that “relationship status” has almost become an identity marker, a reflection of your social capital, your confidence, and your manhood.

Or, as Yael Goldstein said when she said that “finding the man of your dreams” was just too good to be true, there really wasn’t any reason to be worried about your partner going out on “dates” with other people.

If you don’t want your partner to be “dating around”, don’t date them. But if you just want to date and get to know someone, having a man who doesn’t give a fuck about your relationship status is just fine.

Of course, men don’t generally have to worry about this dynamic.

When women have more socially developed feelings and motives, or when women are used to being the ones in control, it becomes a little awkward to get into a relationship that is more than a little unequal.

I’ve been on many first dates that were peppered with questions like “What do you do?” “Where do you live?” and “How long have you been single?” and it’s an uncomfortable feeling because I don’t know enough about these guys to answer and they don’t know enough about me to get to know.

Sometimes it’s a bad idea to date a guy who hasn’t really gone out with other girls. However, even on a good first date, this is a bit like asking a woman what she does for a living or whether or not she has a boyfriend.

So it’s worth bringing up and listening to if you can. It’s important to recognize that sometimes you’re on the way to a relationship and other times, it’s just a first date.

If a date goes well and you want to get to know someone better, it’s a good idea to bring up plans.

When they’re nice enough, men like to hear about your work, your other hobbies, your ambitions.

What men want from a relationship

With Your Friends

There’s a reason that most straight men consider a lot of romantic behaviors (for example, kissing, intimacy, and cuddling) to be annoying, if not uncomfortable.

The more these things you want, the more they want. And men are not the only ones who feel this way.

There’s a reason that after sex, most women feel like they have to check out and shower right away.

Why? Because sex is a totally beautiful, intimate experience for a woman, and she would like to enjoy it in silence.

Most women don’t really enjoy getting their hair or makeup done, or wearing uncomfortable clothing that won’t get sexier.

Women want sex to be a completely positive and fun experience for them, and even if it’s not great sex, they usually just want it to be good enough that it’s worth their while.

Because we’re not used to having this kind of conversation, many women are surprised to learn how many things they enjoy and would like to engage in.

And it’s the very same qualities that are attractive to men that are also attractive to women.

So when you and a guy are first getting to know each other, it’s good to ask them what they’d like to see more of.

This conversation is also a way for you to check if he’s really interested in getting to know you better, or if he’s just there for the sex (and you already know the answer to that).

It’s very tempting for men to try to act like they are really into you, just so they can have sex.

Women like a man who’s game for them. But if he won’t give a damn about your relationship status, then he probably won’t be interested in getting to know you as a person.

If you see him flirting with other women, he’s not the one for you.

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