Guy friend who once set me up with his buddy now says he might like me—how seriously should I take this?

[Anonymous]

So they added me on facebook recently after a while of not really talking to each other, and I add him back. All fine and dandy, of course. Last night/today we had a conversation that somehow lasted an entire 13 and a half hours and both forgot to sleep- over vc, mind you, he's in another state. We somehow didn't get off the phone until he had to go into work. During this conversation they said they wanted to get to know me better and we decided to use never have I ever as a topic starter, looking up or thinking of various questions. We also went back and forth about a bunch of songs we both like and different games we play, relationship histories, embarrassing moments, all kinds of fun bullshit. Then they said that they were going to embarrass themselves and said they might actually like me, continuing with that they weren't entirely sure, that he thought me cute and fun to talk to- that he didn't approach because he was trying to set me up with his buddy who really liked me at the time- and wanted to ask a lot of questions to know me better. Playing never have I ever he mentioned sunburns, and I replied that I had em a couple times, but don't have enough melanin to completely avoid it, to which he said that he could give me some, before quickly brushing it off, calling it a reflex, so I just rolled my eyes and said he wouldn't be the first (to say that), and he said that he wouldn't mind being the last? Anyway, I replied that I doubt he'd be the last to say it, since a lot of people like to talk shit, and he paused and asked whether I thought he meant it or not. I said probably not, since he called it a reflex, then he asked if I remember what he said earlier, possibly about how he said he liked to be straightforward? (He didn't elaborate on that bit, guessing) I'm somehow at a loss, we had some great conversations so far, and that last one was over half a day, but we also haven't been back in contact that long, so I don't know if he's actually serious?

[HollyK21]

I think we can establish that he’s at least interested, so if I were you, before things went any further I’d be asking what his intentions are, and how this would work. He’s playing it safe by keeping you at arms length, and it could be due to the distance if we’re being honest. So what would be the workaround for that? Would you be willing to travel, or him? As someone who has also innocently started talking to a guy before it turned into an LDR, I get not wanting there to be any pressure, even feelings of uncertainty about your own feelings. However, I think that diving deeper and allowing your feelings for him to grow before establishing if he’s even worth the investment, could ultimately end up with you being either hurt or disappointed if you later found out he ultimately isn’t interested what comes with maintaining an LDR. So before you take it serious, ask the right questions.

[Asker]

So I'm actually going into the Navy boot camp in 2 weeks, I'm not going to have too much traveling freedom for a while, and he recently moved to where he is now, so I'd say it'd be a little difficult at the moment at the very least, but we were pretty good friends even though we didn't talk to much before-perhaps, like he said, he was mostly just trying to not get too close with his friend's crush, but we were both in dorm leadership and student government as well as having other mutual friends. While I don't have a lot of travel freedom yet, I'll have to see how much I have in the future. Do you have any specific questions you would recommend starting off?

[HollyK21]

I wasn’t always straightforward due to my concerns over chasing the guy off, not wanting to seem pushy and all that. But towards the end of my dating efforts (I’m engaged now), I would ask: “what are your intentions for talking to me?” And in your situation, I’d include: “Could you see this going anywhere, given our circumstances?”. I feel like once you start delving into the realm of talking hours upon hours, establishing interest, flirting, etc, it is no longer a fully platonic connection, because friends don’t really do that, and men don’t really invest like that into women they see nothing in. What you don’t wanna do, in my opinion, is to keep putting efforts, energy and emotions into that connection if ultimately he’s just looking for a penpal. You don’t lose anything by seeing where his head is at, and I think it’s actually quite mature to cover those bases. It’s not like you’d be asking for a full blown relationship right away, but just assuring that you are intentionally working towards something.

[Anonymous]

It’s actually possible. It just took him seeing someone else w you to realize it. It’s possible he may have had those feelings all this time but was confused until he seen you w another man. Maybe he was just nervous about telling you. How did he tell you this? He just came out and said it? In person? Text? Phone call?

[Anonymous]

Not very.