"Since we're both single, and you're in town, why don't we ..."

“It’s occurred to me that we’re both single, and I realize that a long-distance relationship is impractical for the two of us. How do you feel about spending our time together similarly to the way we did during the summer when we first met? We can see the sights, eat well, and spend the nights making love. I assume it’s at least been several months for you, and I haven’t as much as held someone since May of 2013. After this, we will go back to our lives, but for now, I’d like to take the opportunity, since that summer is one of my happiest memories.”

My therapist says that I sounded completely genuine, authentic, and sincere when I said that, and thus I should simply say it to the object of my affection (R.) when R. comes to town soon, for several days. My therapist adds that R. almost surely already knows how I feel. Another friend, who is one of the closest people (along with R.) I’ve ever had to a Significant Other, essentially agrees.

I’m a bit gobsmacked by this. I want to make it clear here that this is an extremely difficult part of life for me, and despite little shyness or reticence on my part I am perennially unsuccessful and involuntarily single. I don’t really understand the norms of this sort of thing, try as I might.

Wouldn’t saying the above potentially disturb R., make it seem like I haven’t moved on from 2002, and potentially jeopardize our friendship forever?

Some details:

*R.'s aunt is my former English teacher, and in the summer of 2002, when we were both 20, R. was house/pet-sitting for said aunt, and I was tasked with giving R. someone to hang out with and have fun in a new city. We proceeded to have the great time mentioned above, which at the time had more emotional significance for me than for R., and subsequently, when R.'s relationship status moved from “ambiguous” to “taken,” my heart broke.

*In the intervening years, we’ve usually remained good friends, but there have been (long) periods in which we’ve been out of touch, entirely due to R. cutting off communication. R. insists (credibly) that that sort of thing is all in the past. Indeed, we’re both clear of the similar unhappy, angst-filled valleys that we were in during and after our college years. Since coming back into my life, we’ve seen one another in person several times, and things have been great.

*Some time in the early summer R. initiated a breakup with a partner of ten years, entailing a move-out (R. had thought they were to be partners for life) and is now thoroughly (and satisfyingly) single for perhaps the first time since age 13.

Thanks in advance for any insight; I really don’t understand this stuff. Way back then, R. told me that “Besides the physical stuff, you were just like another of my good friends.” At the time, that hurt, but now, I’m all for it. The question is, will asking for that be a huge gamble? R. is one of my favorite people in the world, and throwing this friendship away is out of the question.

Well. . . I think you should try to assess in the moment whether R is open to that kinda thing. Maybe you could just reveal a little at a time and try to get a sense, and it might be obvious as soon as you guys meet again.

So, basically try to test the waters and find out the temperature before jumping in.

But, if it’s really what you want maybe you should be more assertive.

Sounds like you want to be a “friend with benefits”. Nothing ventured, nothing gained. If you don’t ask, the answer will surely be no.

Sorry to up the ante here but it seems to me OP stands to lose a friendship he values.

Well then you qualify the request, that the friendship is more important than the invitation, so even if it is turned down the friendship is paramount, but on the chance that they are on the same page, they didn’t want to miss out on the opportunity with them.

Yes, thanks, I should have included that. "Our friendship is definitely more important than this … "

How awkward (or not) is all this?

Not exactly the same scenario, because we’d never had an intimate relationship at all before, but about 12 years ago, my long term friend came to visit me when I was in Virginia at my Army OBC. I’d had a crush on her in high school, but nothing ever came of it, and we were just close friends. She came down, we shared a very nice several days, with no real intamacy or anything, but sparks flew in my mind. I debated the same thing. I was planning on spilling my guts to her, despite the fact that I was moving to Germany for 3 years in just a few months…just to take a shot. I was terrified of making that jump and losing the friendship too.

She beat me to the punch, though, and laid a similar thing out to me a few days later, and was likewise terrified of ruining our friendship. Well, we’ve been married 11 years and have two kids together. Not saying that’s how it’ll work out for you, but if you are really good friends, and she doesn’t feel the same way, it’ll be awkward for a bit and then you’ll recover. But given that another very close friend says go for it, you’re probably going to be just fine.

If it does end up just being a nice friends with benefits fling, then fine…if it leads to more, then great. You don’t have a lot to lose. My dad pushed me in 8th grade when I first contemplated asking a girl out (that girl was actually my wife, but anyway)…“If you ask her out and she says no, you’re in the same position you are if you don’t ask her.” He was right. She said no, but we still stayed friends, and well, it took a while, but eventually I wore her down. :smiley:

If you really want to do this, do it…luck favors the bold. (Oh, and by the way…my wife is an R.)

Only as awkward as you make it.

It sounds like you’ve already been intimate. Sounds like your friendship survived it. I see no reason it won’t continue to survive it as long as you’re both on the same page and are very honest about your expectations (and when those change).

Nothing ventured, nothing gained.

Good luck.

As I understand it, the socially correct thing to do is to not explicitly say any of this.

You ask him or her “hey, you’re in town, let’s hang out…”

Once you’re hanging out, if he/she is wearing a seductive outfit and acting a certain way, that’s a message all in itself.

When the outing ends and it’s time to have sex, you say “hey want a quick nightcap before you go?”

And so forth. The reason for all this dancing around is that women are wired to be reluctant to have sex. They take a huge risk in doing so, at least over the last few thousand years, so they are innately reluctant. It has to happen “spontaneously” as you “sit on the couch” having that nightcap and end up making out which leads to sex.

The thought is fine. I agree with the “see where the night takes you” approach, though. Why try to write a story’s end before the first chapter?

That is ridiculous pseudoscience, as anyone who has ever been to a college party can tell you.

Apparently Habeed’s experience only comes from watching American movies.

I think you should bring it up in a joking manner after you get her back at your place

“Hahaha. Remember when we were young and stupid and used to hook up?”

This brings up sexual memories involving you.

In her mind she’s already sleeping with you. Just gotta go for it.

All this asking-and-talking-about-it stuff will just kill the mood.

You know, if when rebutting a general proposition, your best shot is to come up with a very specific circumstance when that proposition is incorrect, you might actually be doing a better job of providing “an exception that proves the rule” than effecting a rebuttal.

Yeah, R. already informed me about the trip, and referenced the great time we had last time.

See, this is the part that has almost always made no sense to me, in this context and others.

Sure, test the waters at first, but by the same token, isn’t open communication usually appreciated? I’m thinking of Jman’s scenario above, and hoping that mature folk like us can take a more direct approach to these things. I mean, do all the various kinds of relationships I read about people having happen spontaneously, or through “dancing around” the issue?

I only went to a few of those, and didn’t learn much.

Same here, to an extent.

Hmm. Don’t make assumptions about the genders of the participants; but in any case, I don’t know if I’ll seem the least bit authentic bringing it up like that.

Even if you do actually discuss it, I wouldn’t do it the way you show in the OP. It seems really stilted and artificial. And needlessly verbose, like you are apologizing for even suggesting the idea. How about something like “I know we live really far apart, but why don’t we hang out again like we did that summer we first met? I think it would be really good for both of us.”

Maybe that’s still a little awkward. But what you’ve written in the OP sounds like a formal request. This is a friend, not your boss at work.