A man I used to be only casually involved with asked to spend time together and is showing a lot of changes in his behavior. How should I proceed to explore this safely?

[Rainyday110]

I (24F) dated this guy (35M) a year and a half ago when I was applying to med school. We were together for about two months before he ended things. He’d asked if I’d stay in our city even if it meant changing my career path. When I hesitated, he said I might resent him one day and that I was too young to make that kind of decision.

After that, we both dated other people but would reconnect casually from time to time. He was stressed about his business, I was busy with grad applications, and the casual thing worked for both of us. He used to ask me to be more emotionally open, but I wasn’t comfortable enough back then.

Eventually I told him I didn’t want casual anymore after I got into grad school in our city and moved on (to be fair he had started asking me out back then but I acted a bit weird and made fun of him and was super guarded so the plan didn't happen). Since then I started therapy, have learned slowly how to be comfortable with vulnerability which has been showing well in my friendships and dating life, picked up new hobbies, and overall became a better person.

Recently, he reached out again. We hooked up once, but this time he was way more present and curious, asking about my grad program, if I’m religious, saying he likes “educated, traditional women.” He told me "something about you has changed you're no longer sharp and don't mask vulnerability with humor, you have become much softer, what are you doing differently?" and that he really enjoyed being around me and loves how I'm feminine and graceful. He also mentioned his business is finally doing great, and that “when men are ready for marriage, they just are they don’t waste time.” . He also asked very detailed questions about my program, the timeline, etc. We also bantered a lot like we always do but it felt just very different than previous times!

He invited me to a morning workout class today, then we grabbed lunch and talked for three hours about careers, values, kids, etc. He said, “Realistically I’d want to have kids in the next two years, I’m aching to have a daughter.” I told him he’d make a great dad and said I also want marriage and kids soon. He also said he's thinking of buying the apartment unit he's in and wants to get a dog once he has a family.

When we said goodbye, he didn’t kiss me at all or invite me back to his place (even though we literally had sex two days before!), just said, “Text me later?” I then sent him a photo of the pastry I baked and said “ I’ll save you one next time!” He said “those look lovey” but nothing more…

Now I’m confused. Is he genuinely seeing me in a more serious light this time, or am I overthinking it? How should I proceed from here?

Edited November 10, 2025 by Rainyday110

[Sony12]

He could be more interested now but there is also a chance he will revert back to how he was before once he gets you in the sack a handful of times again. You will just have to see how it goes. It isn't uncommon for guys to try to get back into contact with ladies they were once having sex with. Many times it's just because they are eager to get laid again.

Edited November 10, 2025 by Sony12

[Sanch62]

2 hours ago, Rainyday110 said:

Now I’m confused. Is he genuinely seeing me in a more serious light this time, or am I overthinking it? How should I proceed from here?

You're the only one here who knows him at all, not us.

How to proceed depends on what you want. You haven't spelled out that part to us. Would you care to?

[Rainyday110]

Just now, Sanch62 said:

You're the only one here who knows him at all, not us.

How to proceed depends on what you want. You haven't spelled out that part to us. Would you care to?

Thank you so much for your response!

I would love to have a serious relationship with him, but I don’t want to tell him this directly because I know he has rejected women in the past and I’m afraid I’ll get rejected. I’m hoping to settle down and also have kids in the next few years so our goals align in that aspect. But in the past he once told me, after I broke up with him for the third time and told him he hurts people (which made him very guarded) that he didn’t develop the romantic connection with me and maybe it was his fault and we had to spend more time together 

[Sanch62]

52 minutes ago, Rainyday110 said:

Thank you so much for your response!

I would love to have a serious relationship with him, but I don’t want to tell him this directly because I know he has rejected women in the past and I’m afraid I’ll get rejected. I’m hoping to settle down and also have kids in the next few years so our goals align in that aspect. But in the past he once told me, after I broke up with him for the third time and told him he hurts people (which made him very guarded) that he didn’t develop the romantic connection with me and maybe it was his fault and we had to spend more time together 

Okay, you've already told him that you don't want casual anymore. So it's up to you to back yourself up by no longer behaving casually. Unless you're willing to do that, it's just noise that neither of you takes seriously.

There are no tricks to convert someone into wanting what they don't want with us. He's stated he's seeking an educated traditional woman. Does he view women who'd casually sleep with him as traditional? He's the only one who knows that, so it's something you can ask him if he ever decides to invite you for an actual date.

If he just contacts you to hook up again, I'd pass. That's not going to buy you anything beyond where you've already gone with him. If he's not interested in dating you for a relationship, hanging around his orbit won't persuade him otherwise. 'Spending more time' is just his carrot to get sex, and that's always worked for his agenda, not yours. Have you noticed?

Edited November 10, 2025 by Sanch62

[ExpatInItaly]

1 hour ago, Rainyday110 said:

after I broke up with him for the third time

Wait, you two only dated for two months and broke up three times? 

Am I understanding that correctly? 

 

[Rainyday110]

Just now, ExpatInItaly said:

Wait, you two only dated for two months and broke up three times? 

Am I understanding that correctly? 

 

So we dated seriously for two months (real dates, no sex, etc) then he ended things because I was in my gap year and unsure if I’d stay in our city for grad school (I was applying all around the country) 

we then both dated other people but he reached out to me again and we started a casual hookup thing (only sex, nothing more, no dates, etc) and then after I got into grad school in my city he asked me out on dinner but didn’t follow through. Then I ended things.
 

We then reconnected again (he texted saying how we were before wasn’t the best etc but again no change in his behavior and I was still guarded as well) and I ended things again. Then again he came back and I ended things again. This last time he came back, we hooked up, and he said he feels I’m different now (which is fair, I’ve been through a lot of therapy and self growth) and asked me out to do the workout clasd and then lunch for the first time since 1.5 years ago basically. 
 

[basil67]

You're 24 and pursuing a medical degree - you've got your whole life in front of you.   Meanwhile, he's 34 and starting to panic about wanting to settle down and have kids.  If you were to follow his path, you would likely never reach your goal of becoming a doctor and it would appear that he doesn't care about this.

Follow your dreams for becoming a doctor and making a career, and if you're going to date, choose men who are your own age.   Have kids when it fits into your schedule

 

[Gebidozo]

It’s possible to get back together with people we used to causally date or hook up with, and start a more serious relationship.

What bothers me in your case is the way he approached you. It looks like he is methodically choosing someone to settle down with. Like he suddenly has this urge to have family and kids, and he thinks you might be a fine candidate.

His speech about what kind of women he likes feels strange, too. When men say they are looking for a traditional woman, it often means the same as when women say they are looking for a nice guy: they are settling for a calculated option instead of naturally pursuing and developing a connection.

It doesn’t feel organic, it doesn’t feel like he has deep feelings for you and is acting on them.

I’d be careful if I were you.

Edited November 11, 2025 by Gebidozo

[ExpatInItaly]

3 hours ago, Gebidozo said:

It doesn’t feel organic, it doesn’t feel like he has deep feelings for you and is acting on them.

That's my impession, too. 

I don't think I'd hold my breath here, OP, especially since the backstory between you two is so shaky. None of it bodes particularly well. 

[MsJayne]

So far you've been smart enough not to get too involved with him. I'd keep it that way. He sounds like the kind of dude who has his life mapped out and is looking for the woman who best fits his requirements for an ideal partner, like it's not about love, it's about filling a role he has planned for you. I'm guessing you're not just above-average intelligence, you're also good-looking, and he sees you as good breeding stock. Steer clear, don't let him derail your career dreams with his plot to have you knee-deep in poopy diapers within two years . 

[Rainyday110]

7 hours ago, MsJayne said:

So far you've been smart enough not to get too involved with him. I'd keep it that way. He sounds like the kind of dude who has his life mapped out and is looking for the woman who best fits his requirements for an ideal partner, like it's not about love, it's about filling a role he has planned for you. I'm guessing you're not just above-average intelligence, you're also good-looking, and he sees you as good breeding stock. Steer clear, don't let him derail your career dreams with his plot to have you knee-deep in poopy diapers within two years . 

That’s very kind of you to say, thank you! And yes, we both went to a very selective school, I’m doing a PhD now and do modeling on the side (he finds me physically attractive, and he usually says it) he’s also super attractive and has a LOT of women interested in him, asking him for exclusivity and his usual reason for rejecting them is that he just didn’t “feel” it. 

He said he’s supportive of me having a career with a good work life balance (which I actually want!) but to be honest with you I also got the sense that he’s just at that stage where he wants to get married and thinks I just fit that role. 

[Rainyday110]

13 hours ago, Gebidozo said:

It’s possible to get back together with people we used to causally date or hook up with, and start a more serious relationship.

What bothers me in your case is the way he approached you. It looks like he is methodically choosing someone to settle down with. Like he suddenly has this urge to have family and kids, and he thinks you might be a fine candidate.

His speech about what kind of women he likes feels strange, too. When men say they are looking for a traditional woman, it often means the same as when women say they are looking for a nice guy: they are settling for a calculated option instead of naturally pursuing and developing a connection.

It doesn’t feel organic, it doesn’t feel like he has deep feelings for you and is acting on them.

I’d be careful if I were you.

Thank you for your advice! His dating history is actually interesting - he got his heart broken when he was in his 20s, then had one girlfriend in his early 30s, with whom he broke up after telling her that he “just doesn’t love her”. He has been dating around for the last four years but hasn’t been exclusive with any woman (we talk a lot to each other about our dating lives and he said he just “doesn’t feel it”) while telling every woman he’s looking for a life partner. 
 

The thing is I knew a man like him who was in my DMs and hitting up other girls even 3 months before proposing to a girl (she was on a visa which was expiring and needed a green card so that might have affected the timeline) she was definitely more of a “safe choice” compared to the other women he dated in the past. And he still follows his old fillings, likes their posts, etc. I’m starting to wonder if this guy is similar to him as well… especially since he tells me he loves that women from my culture are feminine and American women aren’t like this

[ShyViolet]

So you dated for only 2 months, and then you had a very on/off casual thing.  Now he's all of a sudden talking about marriage and kids.  This is weird when he hasn't even put in the time to show that he is capable of seriously dating you for any substantial stretch of time.  That would be what should come first, before all of a sudden talking all this talk about marriage and kids.   It sounds like he just realized that he wants marriage and kids, and he sees you as someone who could be a top candidate for that.  Instead of really wanting to cultivate a serious relationship with you.  I would be careful and please do not rush into marriage and kids.  A solid relationship needs to come first, which there is not with this guy.

[Gebidozo]

10 hours ago, Rainyday110 said:

he tells me he loves that women from my culture are feminine and American women aren’t like this

In many cases, when a man says something like that, what he actually means is “American / Western women scare me because they are independent, what I want is a submissive wife who’ll make me a priority over her career or any other aspect of her life”.

I don’t know the guy so I don’t want to be unfair or judgmental, but I really advise you to be careful, especially considering the fact that you’re very young.

[Bassthumper]

He got what he wanted...

and got you baking....lol...wow

 

[Rainyday110]

2 minutes ago, Bassthumper said:

He got what he wanted...

and got you baking....lol...wow

 

I did not bake for him! 
we hooked up on Thursday, he asked me out on a day to a workout class then lunch on Saturday, we spent time there for three hours, he didn’t kiss/didn’t make a move. I came back home and baked for myself! (And sent him a photo of it)

[Guest]

So I dated this man 1.5 years ago for two months then we broke up and started casually seeing each other every other week or so just for sex Towards the end, he was inviting me out to dinner, having dinner with me at his place, watching shows, hinting at wanting to take me out but it kind of never happened. I ended things with him but we recently reconnected.

We hooked up last weekend, then he invited me to go to a workout class with him and then we grabbed lunch after. He talked about his life goals, wanting kids, etc and asked about my grad school timeline. However, I didn’t think much of it since he didn’t ask for another date and didn’t invite me back to his place and didn’t even kiss me.

Yesterday he texted me I went over and we hooked up. When we were cuddling after he suddenly asked me “why do you like me? Why do you keep seeing me?” I told him the reasons and then jokingly told him “I know you see me just for the sex” he said no I’m not shallow. The sex is good but you’re very interesting and I like spending time with you. I said yeah we have hot sex. He said yes but I feel lately it’s been more than just sex for both of us. Like that time we grabbed lunch we didn’t have sex didn’t do anything physical but I liked it. I enjoy spending time with you I don’t know yet to what extent but wanted to tell you where I’m at. I said pinky promise me that if you get serious with another girl you’ll tell me (and vice versa) he said of course I will, I just haven’t felt emotionally strong for any woman in the past 4 years.

He then opened up about his past relationships, asked me if I’ve ever been in love, if I’d ever stay with a man I didn’t truly love, etc. the conversation was so relieving and not awkward at all and we both felt so calm afterwards.

But now I’m kind of wondering if he had this conversation to kind of tell me let’s keep it casual and not catch feelings? Or he’s open to exploring more?

[ShyViolet]

1 hour ago, Anonymous said:

But now I’m kind of wondering if he had this conversation to kind of tell me let’s keep it casual and not catch feelings? Or he’s open to exploring more?

I'm not sure why you would think this.... from everything you said it sounds like he is interested in it being more.

Are you interested in actually dating him and it being more than just FWB?

[Anonymous]

2 minutes ago, ShyViolet said:

I'm not sure why you would think this.... from everything you said it sounds like he is interested in it being more.

Are you interested in actually dating him and it being more than just FWB?

Yes definitely I do. I would love to settle down with the right man and I’ve been going on a lot of dates recently although I get along the best with this guy. 

The reason why I’m scared is that when I ended things with him last time over phone, he told me he just didn’t feel anything romantic for me and that maybe it was his fault and we needed to spend more time together. So I’m afraid he’s playing me or that he doesn’t actually like me, although my intuition keeps telling me he’s catching feelings 

[ShyViolet]

5 minutes ago, Anonymous said:

The reason why I’m scared is that when I ended things with him last time over phone, 

Why exactly did you end things with him before?

[Rainyday110]

Just now, ShyViolet said:

Why exactly did you end things with him before?

So the first time we were seriously dating things ended because he asked if I’d change my career path to stay in our city if I didn’t get into grad school here. I kind of hesitated then said yes but he said he didn’t want me to resent him one day.

 

then I got into school in our city. During the whole application cycle I was seeing him casually having sex etc. Then he had initiated more intimate conversations like he’d ask me to be more vulnerable and sweet to him, he’d say things like “I can’t take you out like this if you were this pretty dress (jokingly)” and after I decided to stay here he said we should grab dinner to celebrate your accceptance. Then he would text me sweetly saying we’ll get dinnner in a week once he’s back from his trip. Then one night I drunk texted him “you’re one of my favorites” (I didn’t want him to know I liked him) and he got mad and said I’m one of many? You have many favorites? Then he never followed up on dinner, distanced himself, so I thought he was playing with me and didnt want anything serious so I ended things

[FredEire]

3 minutes ago, Rainyday110 said:

So the first time we were seriously dating things ended because he asked if I’d change my career path to stay in our city if I didn’t get into grad school here. I kind of hesitated then said yes but he said he didn’t want me to resent him one day.

 

then I got into school in our city. During the whole application cycle I was seeing him casually having sex etc. Then he had initiated more intimate conversations like he’d ask me to be more vulnerable and sweet to him, he’d say things like “I can’t take you out like this if you were this pretty dress (jokingly)” and after I decided to stay here he said we should grab dinner to celebrate your accceptance. Then he would text me sweetly saying we’ll get dinnner in a week once he’s back from his trip. Then one night I drunk texted him “you’re one of my favorites” (I didn’t want him to know I liked him) and he got mad and said I’m one of many? You have many favorites? Then he never followed up on dinner, distanced himself, so I thought he was playing with me and didnt want anything serious so I ended things

I wouldn't blame him for having a bad reaction to that text, personally.

From OP it sounds like you are on the same page in terms of getting more serious. It seems a bit of a red flag though that he wasn't serious about you before and now suddenly seems to be.

It could be that his feelings have changed, or that he likes the idea of having a woman in love with him but isn't being honest. The only way to really know is try it and see how it feels for both of you. Yes there is the risk of getting hurt but that's life and love.

[flitzanu]

1 hour ago, Anonymous said:

I enjoy spending time with you I don’t know yet to what extent but wanted to tell you where I’m at. I said pinky promise me that if you get serious with another girl you’ll tell me (and vice versa) he said of course I will, I just haven’t felt emotionally strong for any woman in the past 4 years.

 

you need to pay attention to this info.

sure, maybe he's being vulnerable and maybe hinting at more, but saying he's not that into you "right now" is still saying a lot, and that's 99% a big "no" and this way he has warned you in case you try to make it into something more than free sex.

[ExpatInItaly]

34 minutes ago, Rainyday110 said:

So the first time we were seriously dating things ended because he asked if I’d change my career path to stay in our city if I didn’t get into grad school here. I kind of hesitated then said yes but he said he didn’t want me to resent him one day.

I remember your recent thread about this man. 

It's been on and off for a while. I am not sure I would revisit this, but for peace of mind, you should talk to him about this and put it to rest one way or another.