[theysayimsmartimnot]

I’m 23 and I met a businessman, who is 40. We went on a date. I found out that he’s only staying in my city for 2 years and then leaves for another place. He’s been changing places like that for 15 years now. Long story short, we slept on that first date. He was clearly thinking that this was a one-time thing, but I thought we could do causal, so I asked him later, he said that he wasn’t looking for a relationship, but would like to see me again. We met again next week. I thought we could do this thing weekly, but he started ignoring me. Then I realised I was the one approaching him, he didn’t text first. But. We met again 3 more times. And at some point he cooked for me, started kissing me a lot, hugged me, slept with me, intertwining his feet with mine. I felt the connection and kept asking myself: does this mean something or is it just my female brain tricking me into thinking like that? Until then I thought I just liked spending time with him, but now I think I’m starting to fall in love. And he’s ignoring me most of the time and I keep being the one making moves. I am the one chasing the guy who seems so elusive. I like the challenge, but I also feel that he doesn’t respect me at all. He sometimes texts me too, sending links to stuff we discussed. But that is rare. And I know he’s sleeping with a lot of different people.
So here is the question. Do I have the chance to turn this casual thing into a serious relationship or at least keep it going? What do I do?

[Sara20]

I think you need to just give up on him and find a different older man if you are interested in them. He is 40 and if he hasn’t been married before and doesn’t have kids by now he is probably just a confirmed bachelor and doesn’t plan on ever doing so and or doesn’t even want / need a girlfriend or any type of friends with benefits. You are better off just seeing him while you can and enjoy the fun but remember not to get emotionally attached. 🙂

[April Masini, your AskApril]

He’s not interested in a relationship beyond casual sex. He’s made this very clear to you. If you want a committed, monogamous relationship, then you should look elsewhere. But don’t make yourself crazy by trying to chase him down and make him change his mind. It won’t work. 😳 And you’ll get hurt in the long run. 😕

[Sally]

That kind of attention can feel really intense, especially when it comes in pieces and then disappears.
Here’s the hard truth, said gently. He told you what he wanted early on. He likes you, he enjoys you, but he’s not looking to build something. The age gap matters here, not because it’s wrong, but because he’s already living the life he chose. Moving cities, keeping things light, not getting attached. That’s not accidental.

The affection you felt was real in the moment, but it doesn’t automatically mean intention. Some people are warm and present without wanting more. That’s confusing, especially when you’re catching feelings.

You’re not wrong for wanting more. But chasing someone who stays distant will slowly wear you down. If you keep going, do it knowing it may never turn serious. And if that already hurts, it’s okay to step back. Protecting your heart isn’t weakness. It’s just honesty.

[Tara]

You’re getting played and confusing intermittent attention with connection. This man told you exactly who he is on day one: transient, noncommittal, emotionally unavailable, and not looking for a relationship. You ignored that because the chemistry felt intoxicating and because you liked the chase. That’s not romance, that’s you projecting depth onto someone who has zero intention of offering it.

Let’s cut through the fantasy. A 40-year-old man who moves cities every few years, sleeps with multiple people, doesn’t initiate contact, and lets a 23-year-old woman do all the chasing is not “elusive,” he’s disengaged. The cuddling, cooking, kissing, and intimacy mean nothing beyond the moment. Men like this know exactly how to create closeness without responsibility. It costs them nothing and keeps you hooked. If he wanted you, you wouldn’t be wondering. You wouldn’t be initiating. You wouldn’t be ignored.

You do not have the power to turn this into a serious relationship. Full stop. There is no strategy, patience level, or emotional availability that will change a man who has built his entire life around avoiding attachment. The more you chase, the less he respects you, and you already feel that, which is why this hurts. “Keeping it going” just means prolonging a dynamic where you give more and get crumbs.

[Member]

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