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 2 hours ago 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 1 hour ago 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