Any thoughts?

[Unsure.com]

Okay, here is my issue. I’ve know this guy for a few years, we work together. We work pretty close together as a team. We became friends, started hanging out with other coworkers and we would text each other almost nightly. One night, while out with a mutual friend. We had too much to drink and ended up making out pretty hardcore, no sex or anything. We talked about it after, through text, but nothing was ever really defined. A few months later, I left the job and shortly after we eventually stopped texting each other, at least not consistently. We kept in touch maybe once per month. I return to the same job and our friendship pretty much picked back up. The other night he text me and asked if I would be willing to come up to the job to help with with something. Okay so first, our job is closed and second, he could’ve asked anyone to help him. I agreed to go and afterward he’s like, thanks for helping me, I owe you one. So, I’m like buy me a beer. He agreed and off to the bar we go. We ended up going to two different bars, then ended up at a lake. We drank beer and went swimming until the park closed. We briefly held each other in the lake but nothing else. The next day at work we didn’t really talk about, except we briefly laughed about a funny incident that happened at the lake. Ugh, I’m just super frustrated and I need advise.

[TheEvilJester]

Honestly... I'm sensing a theme here. You two hit it off... you two do something that at least hints that the feelings on both sides are romantic and not just friendly.... and then you two completely avoid talking about it. I don't mean to make it sound like I am over simplifying things.... but I think your path forward is pretty obvious. Talk to him about all this. It would be nice if things were natural and clear. If he asked you out, making clear it was a date, and things progressed as you'd expect.

But, it sounds like that hasn't happened. Things have remained ambiguous. Any time one or the other of you made any kind of move it wasn't clear if it was just a friends or meant something more.

Do you want to date him if he's interested? Or do you only like him as a friend? Think of that before you even bother to proceed, because how you feel on that will inform how you handle it if/when you proceed. But, either way you should talk to him. Make your intentions clear and ask if he is on the same page. If you two keep dancing around it, how do you ever expect anything to become clear? Believe me, I understand it can be hard to bring yourself to have that conversation... but if he's not making things any clearer, how will you ever know unless you ask?

Good luck.

[Unsure.com]

I know your right and I should talk to him about it. I just don’t get why it has to be so difficult. I’ve never had this happen before. In the past, when a guy likes me, he lets me know.
Ugh, I guess I will have to suck it up and find the courage to talk to him.
Thank you for your help!

Honestly... I'm sensing a theme here. You two hit it off... you two do something that at least hints that the feelings on both sides are romantic and not just friendly.... and then you two completely avoid talking about it. I don't mean to make it sound like I am over simplifying things.... but I think your path forward is pretty obvious. Talk to him about all this. It would be nice if things were natural and clear. If he asked you out, making clear it was a date, and things progressed as you'd expect.

But, it sounds like that hasn't happened. Things have remained ambiguous. Any time one or the other of you made any kind of move it wasn't clear if it was just a friends or meant something more.

Do you want to date him if he's interested? Or do you only like him as a friend? Think of that before you even bother to proceed, because how you feel on that will inform how you handle it if/when you proceed. But, either way you should talk to him. Make your intentions clear and ask if he is on the same page. If you two keep dancing around it, how do you ever expect anything to become clear? Believe me, I understand it can be hard to bring yourself to have that conversation... but if he's not making things any clearer, how will you ever know unless you ask?

Good luck.

[Hooo!]

So maybe the guy is either just shy or inexperienced or tiny dick?

[TheEvilJester]

I know your right and I should talk to him about it. I just don’t get why it has to be so difficult. I’ve never had this happen before. In the past, when a guy likes me, he lets me know.
Ugh, I guess I will have to suck it up and find the courage to talk to him.
Thank you for your help!

Oh, I am absolutely right there with you. It shouldn't have to be so hard. And, truth be told, MAYBE the reason it seems so hard this time is because he's not into you after all. But, by the same token, MAYBE he is and there are just other reasons he hasn't made things more clear/easier.

He could be really shy. I could certainly relate to that. I'm ridiculously shy myself. Thing is, even with how shy I am, if a gal and I seemed to really be hitting it off, I'd eventually at least do SOMETHING. Maybe I'd flat out just ask her out on a date. Maybe I'd be a little more subtle if I wasn't yet sure enough to be that bold... but I'd at least do something to make it seem obvious I am interested and get an idea if the feeling seemed to be mutual. So, if this guy truly is just shy then he is like the world-leader in shy. LOL!

But, if you are interested in him if the feeling is mutual, then it could be worth it to at least try. I definitely agree with you that it would be nice if it were easier. But, so far he hasn't made it easier, so you may just have to go for it or otherwise you may just be left wondering. I will say this, though.... let's pretend the best case scenario. Let's pretend he IS very interested but was just too shy. Let's pretend you ask him out and things go well...

That's great, and if he's truly super shy it make continue to take a little extra effort from you to get things moving along. That's fine TO A DEGREE. Just be careful that it doesn't wind up feeling like it is always all effort from your side only. That it doesn't feel like you are basically having to drag him every step of the way through a relationship. I can absolutely feel for shy people (if that does, indeed, turn out to be the case with him), but at some point even us shy peeps have to learn to step up.

Best of luck to you either way.