How do I broach this conversation?

So over Thanksgiving I reconnected with a man with whom I was very, very close from the end of high school through my junior year of college. Long story short, our friendship turned into a fling. We agreed to try to make it work when I went back to college, but he just disappeared into the wind. Fast forward five years, and around February of this year, he reached out to me on social media. We chatted a bit and caught up. Before Thanksgiving, he asked to get a drink with me. I agreed. When we met up, it was like we were never apart. Him and I have always had really great chemistry and get along incredibly well. I ended up spending most of my time back in town with him and his family (his family has always really loved me. We grew up in a very small town so everyone knows everyone). Since coming back, he has been in constant contact with me, and he is coming to visit me this weekend.

I want to know how to bring up the subject of what exactly he's looking for, but I don't know how without looking like a creep or clingy. I just want to know what exactly I'm getting myself into mostly so I can adjust my expectations accordingly. Any advice?

Thank you!

After one reunion drink together you may want to do more catching up and play it by ear. For example, is he in a relationship?

It sounds like he's interested in you but one drink is not enough time to ask him to view into the future like a crystal ball. Let things unfold naturally as you get reacquainted.

When we met up, it was like we were never apart. I ended up spending most of my time back in town with him. he is coming to visit me this weekend.

He is coming to visit you for the weekend? So what's the plan there? Is he staying with you?

I think it's fair game to bring up the conversation in general about where he is at in his life and what he is looking for at this point in time - dating around for fun, dating that leads into an LTR, etc. I would just emphasize in general terms not specifically about you because it's simply too early for that.

Also, have you addressed his disappearance back then and what happened with that? You say that you have this great connection but that's not consistent with his previous behavior. Meaning that the connection you feel could easily be one sided. I'd explore that if I were you so you don't over invest in this in case it is one sided.

After one reunion drink together you may want to do more catching up and play it by ear. For example, is he in a relationship?

 

It sounds like he's interested in you but one drink is not enough time to ask him to view into the future like a crystal ball. Let things unfold naturally as you get reacquainted.

Oh I'm certainly not saying i want to be in a relationship with him right now, I just want to know if he's looking to just maintain our friendship or begin dating, so I don't get attached to him again.

He is coming to visit you for the weekend? So what's the plan there? Is he staying with you?

 

I think it's fair game to bring up the conversation in general about where he is at in his life and what he is looking for at this point in time - dating around for fun, dating that leads into an LTR, etc. I would just emphasize in general terms not specifically about you because it's simply too early for that.

 

Also, have you addressed his disappearance back then and what happened with that? You say that you have this great connection but that's not consistent with his previous behavior. Meaning that the connection you feel could easily be one sided. I'd explore that if I were you so you don't over invest in this in case it is one sided.

Yeah we talked about it. The first thing out of his mouth when he saw me was how he was so sorry for treating me like that, that he was young and dumb (we were 19 at this point) and that he's really fortunate that I was even willing to allow him to apologize.

So you think it's ok for me to ask generally if he's looking to date casually or looking for a more serious relationship? I just don't want to overstep my bounds or come on too strong, because like I said, not trying to jump into a relationship with him, but I do want to know what his intentions are.

Yeah we talked about it. The first thing out of his mouth when he saw me was how he was so sorry for treating me like that, that he was young and dumb (we were 19 at this point) and that he's really fortunate that I was even willing to allow him to apologize.

 

So you think it's ok for me to ask generally if he's looking to date casually or looking for a more serious relationship? I just don't want to overstep my bounds or come on too strong, because like I said, not trying to jump into a relationship with him, but I do want to know what his intentions are.

like others suggested, it's more than okay to ask what his intentions are in general terms, not specific to you.

We agreed to try to make it work when I went back to college, but he just disappeared into the wind. Fast forward five years, and around February of this year, he reached out to me on social media.

You have to first go back to the beginning. Why did he ghost you? He can't just come rolling back into your life again, without first explaining why he left you. He should have told you why during your outing. If he didn't, then something is wrong. That is what you should be focused on.

You shouldn't have him feel that he can come and go as he pleases, with no explanation.

You have to first go back to the beginning. Why did he ghost you? He can't just come rolling back into your life again, without first explaining why he left you. He should have told you why during your outing. If he didn't, then something is wrong. That is what you should be focused on.

 

You shouldn't have him feel that he can come and go as he pleases, with no explanation.

Yeah we talked about it. The first thing out of his mouth when he saw me was how he was so sorry for treating me like that, that he was young and dumb (we were 19 at this point) and that he's really fortunate that I was even willing to allow him to apologize. This was 5-6 years ago, so we are obviously both at very different points in our life. I'm just wondering how I discuss what his expectations are without sounding overly eager.

Let him discuss his expectations. Interrogating is probably not a good choice, it sounds desperate. Kinda weird to discus expectations and "what are we" after one drink, no?

Simply converse naturally and everything you need to know will come out in time. What's the rush? Anxiety? Curiosity?

how I discuss what his expectations

Let him discuss his expectations. Interrogating is probably not a good choice, it sounds desperate. Kinda weird to discus expectations and "what are we" after one drink, no?

 

Simply converse naturally and everything you need to know will come out in time. What's the rush? Anxiety? Curiosity?

I'm don't mean this rudely, but I don't think you've read my posts. This was my very, very close friends for years before we had a fling. When we reconnected, I spent 3-4 hours a day with him for a week and it felt like we never were apart. It's not that I want him to commit right now, I just know because of our past that I'm going to get attached, so I want to know if his intention is to try to keep me as just a friend or date me. There's no rush, just some rationality on my part of knowing I'll get attached and wanting to know if I should cut him before that happens again.

Yeah we talked about it. The first thing out of his mouth when he saw me was how he was so sorry for treating me like that, that he was young and dumb (we were 19 at this point) and that he's really fortunate that I was even willing to allow him to apologize. This was 5-6 years ago, so we are obviously both at very different points in our life. I'm just wondering how I discuss what his expectations are without sounding overly eager.

Don't fixate on it as such. It's more like out of conversation really. Where you are both at in life, dating, relationships, plans. If you start the conversation in that direction and then listen carefully to what he is telling you about his life and future plans, it will tell you all you need to know. It's not really a question and answer type thing. More just talking at large.

Like if he starts telling you how he is starting up a business and he has this plan and funding and a partner and they are going to do x,y, z, then realize that his mind is not on marriage and kids or even serious dating or relationships. He won't have time or focus for that. On the other hand if he is looking to buy a house fit for a family... You get the idea. Listen carefully and stay neutral. Let him tell you.

I'm don't mean this rudely, but I don't think you've read my posts. This was my very, very close friends for years before we had a fling. When we reconnected, I spent 3-4 hours a day with him for a week and it felt like we never were apart. It's not that I want him to commit right now, I just know because of our past that I'm going to get attached, so I want to know if his intention is to try to keep me as just a friend or date me. There's no rush, just some rationality on my part of knowing I'll get attached and wanting to know if I should cut him before that happens again.

If you choose to fall for him that's up to you. But asking him "what's your intention" is probably not a good idea. How would he know? Maybe he just wants to go with the flow. Your pushing for answers without just enjoying the romance.

If you choose to fall for him that's up to you. But asking him "what's your intention" is probably not a good idea. How would he know? Maybe he just wants to go with the flow. Your pushing for answers without just enjoying the romance.

Except there's a difference between pushing for answers and wanting to know if he's just looking for a friends with benefits or a relationship, no?

Except there's a difference between pushing for answers and wanting to know if he's just looking for a friends with benefits or a relationship, no?

Instead of settling for whatever he wants, consider that you have some power in deciding on what you want. If you want a relationship, then allow for dating to carry on and keep things out of the bedroom for awhile. Until you have a good idea from his actions at large where he is at in life and where his head is at with you in particular. Slow down and enjoy the ride. Don't be afraid to create some boundaries and ask for what you actually want and stand by that. Don't have a fling when you want a relationship. It's on you, not him.

You don't need to sleep with him to date him. This time don't have a fling, but go on dates and have fun in other ways. If all he wants to do is sleep with you, you will know soon enough. If he enjoys your company and you feel in your gut he really likes you this time round and it could go somewhere then ask him. You should just see how things go and guard your feelings incase things don't work out.

Your are correct I missed the part that you were already intimate. So that explains why you are eager to know where things stand now?

Except there's a difference between pushing for answers and wanting to know if he's just looking for a friends with benefits or a relationship, no?

You've got some good answers already. But I just wanted to say that regardless of how close you've been in the past, it's just too soon for this. I don't see how you can find out if he wants to date you, or have a fwb situation, or what any of his intentions are without wording it in a way where he won't now EXACTLY what you're doing. He might be able to tell you're trying to get information out of him in a passive aggressive way.

Leave this alone for now and just enjoy spending time with him. And instead of trying to find out if this will turn into a relationship, just wait and see if it does!!

What do you mean by "attach"? I think it is legitimate to wonder if he is someone in whom you want to invest, and he can tell you whether he feels open available and interested in investing in someone else.

Often times when we say attach, we mean, "I expect you to be here; don't leave me." Try to let yourself let go of this sort of attachment regardless of his intentions. Trust that the future will arrive on time, let future visions go. They provide only an illusion of security. Nobody else can be your foundation.

What do you mean by "attach"? I think it is legitimate to wonder if he is someone in whom you want to invest, and he can tell you whether he feels open available and interested in investing in someone else.

 

Often times when we say attach, we mean, "I expect you to be here; don't leave me." Try to let yourself let go of this sort of attachment regardless of his intentions. Trust that the future will arrive on time, let future visions go. They provide only an illusion of security. Nobody else can be your foundation.

Attachment as in having emotional feelings for him. I just think that one knows whether he's, in general, open to a relationship or just wants something casual. All I want to know is whether he's open to a relationship, because if he's not, I don't want to get any closer to him.

Attachment as in having emotional feelings for him. I just think that one knows whether he's, in general, open to a relationship or just wants something casual. All I want to know is whether he's open to a relationship, because if he's not, I don't want to get any closer to him.

I think your approach is all wrong. How can one know if they are looking for a relationship? Maybe he just enjoys your company and just wants to date you. Maybe he's seeing how things go before he takes it to the next level. You want the next level now! He's not there yet. You know what your looking for, but you should just ease up and let him come round to the idea of "a relationship' when he's ready not when you ask straight away. It's the equivalent of walking into a shoe store, and trying on shoes and eying up the ones you want, and trying them on, and the salesman wants an answer straight there "are you buying these or what?"

I think your approach is all wrong. How can one know if they are looking for a relationship? Maybe he just enjoys your company and just wants to date you. Maybe he's seeing how things go before he takes it to the next level. You want the next level now! He's not there yet. You know what your looking for, but you should just ease up and let him come round to the idea of "a relationship' when he's ready not when you ask straight away. It's the equivalent of walking into a shoe store, and trying on shoes and eying up the ones you want, and trying them on, and the salesman wants an answer straight there "are you buying these or what?"

Again, I'm speaking generally, not about whether he wants to commit to me right now. We all know whether we want a relationship or a friends with benefits when we begin dating, we just don't know if we want it with the person we are on a date with.

Again, I'm speaking generally, not about whether he wants to commit to me right now. We all know whether we want a relationship or a friends with benefits when we begin dating, we just don't know if we want it with the person we are on a date with.

Most of my life I thought I wanted a rl. I was wrong. Now - to Jagger's point: With the right man I don't care what it is. With the almost good enough man? I don't even want coffee, even if he turns me on.

Ask me what I want and I have 50 answers concurrently. None of them serve your purpose of deciding whether I'm a worthy risk. Only time answers that question.

In my experience those who know they are looking for something more serious make it very clear early on. They don't leave it in the air for you to guess and potentially misinterpret their intentions ( to date with the aim of finding a partner).

You've hung out, slept together, and are wondering what he wants. Based on his actions he either doesn't know, or he's fine with casual or whatever may come or not come of spending some time together.

If you are worried about getting attached and you want more, slow this all down. Don't be in constant contact. Go on dates, real dates where it's crystal clear that's what it is. Stop getting into bed with him right now, wait til you are more comfortable with knowing.

I'd consider it FWB at this point. You sleep together, enjoy time together, but everything else is left unsaid. Actions kind of really say it all.

IAG is dead on. If you ask me Why am i dating, now i will say to find someone with potential for an ltr, with no interest in sticking around if we've no potential. I would have said that when i was unstable, also, so im not sure how valuable are the words.

Actions are huge.

Make sure you commit to yourself before anyone else.

How far away does he live?