How do I set this guy up without making him uncomfortable?

In My Humble Opinion
1

Okay, so I have this former work acquaintance. Very, very nice guy. Sweet, sensitive, wonderful sense of humor, and really cute. He’s single, too, and doesn’t want to be. Anyway, he asked me a couple of days ago if I knew anybody he could go out with. I know of several people, both female and male he could got out with.

My problem is this: I’m not certain of his orientation. The only relationship he has spoken about to me has been with someone named Terry, which is a pretty gender-neutral name. While I realize that this in and of itself does not mean he’s gay, he has never talked about Terry as a woman, instead calling this person “they” or “them” when referring to Terry. In other words, I ask, “So, where you did you meet Terry?” Instead of saying, “I met him/her at this bar,” he answers with “I met Terry/them at this bar, then we started going out, but we had some stupid disagreements and I asked them never to call me again,” never referring to the person’s gender.

Anyway, I’ve got several single friends, male and female, who are looking for a nice guy to go out with, though I think he would get along best with one of my single male friends. Not because they might both be gay (that’s like saying, “Oooh! You’re married to an Indian man! My girlfriend’s mother’s friend is Indian. You would have so much to talk about!”), but because they’re interested in the same things (guitar music, both are graphic artists, have similar backgrounds, and both are huge Madonna freaks, etc.), and they have similar personalities. Both are drop-dead gorgeous, too, but that’s from a straight female perspective.

Anyway, I wish I could find out if he were gay or not without putting him into some horrible, awkward position. I’m wondering if I should just introduce them to each other in a comfortable, group setting without making it a set-up. That way, if they hit it off, they can be friends or whatever else they want to be.

I know I’m probably sounding like a jackass here, but I’m not quite sure what to do. We only worked together for less than a year, and even though we’ve gone out for drinks intermittently since then, I haven’t hung out long enough with him to feel comfortable just asking him. Any suggestions?

2

I find the situation to be embarssing for you, but ultimately harmlessly so. If he asked you to set him up he is assuming that you already know his orientation.

Next step is the laughing admission that you knew he dated Terry, but you never got up the nerve to ask whether Terry was male or female. As long as it is clear to him that it doesn’t matter either way to you, I can’t imagine the consequences will be any more dire than a shared laugh.

You have me perplexed though with the third paragraph. If he is asking you to set him up you have to assume he means in a romantic sense. How can you do that if you don’t know the orientation of both parties? If you are going to set him up with a single male friend of yours it would be disconcerting if one person thinks they are meeting as friends, and the other is looking for more of a soft music and candlelight thing.

I am a bit jealous, I have always wanted to play matchmaker, please let us know how this works out.

3

ask him what happened between him and Terri/y.
or ask him what he likes in a partner. Hell probably use the words her/him that will tip you off.

4

This was going to be my suggestion too. Maybe start off with, “You know what? I know a couple of people who remind me SO much of you, I’d love to hook you up with them. What kind of person are you interested in?”

Good luck, let us know how it turns out!

5

I know - I can’t really set them up romantically without some indication of his orientation. I was trying to duck responsibility. I suppose I figured if I set it up in a non-threatening, casual manner, they could sort of figure out for themselves if they wanted to go out with each other. And if it turns out they don’t, at least they’d have a good conversation at least. Though I see your point - without knowing his orientation I’m doing him, and potentially the other guy a great big disservice. And potentially setting one or both of them up for some big-time embarrassment of their own. :smack:

I guess I should ask. He’s a really nice guy, so he probably won’t get upset, regardless of his answer.

6

You could also just invite all the people you think he might hit it off with and him to go out together some time - to a bar, to a movie, bowling, whatever floats your boat. Then he can pick out just who he likes and take it from there.

7

I’m thinkin that if he didn’t make it clear he was gay when he asked you to set him up you probably can assume that he is straight. To be sure how about a “I know this sounds stupid but are you gay?” He will probably laugh and say no. Then you say thats what I thought but I wasn’t sure Terry can be either. Then you both have a hearty laugh about it.

8

Get him a date with Pat.
ducks and runs

9

My wife pointed out where I went wrong in my assumptions. I read it as you not being sure of the orientation of either person. I now assume that you know that your friend (the potential guy you could set him up with) is gay, the only questions is about your co-worker.

I was picturing either a reality show or a wacky sit-com episode come to life.

10

The OP was quite a bit different from what I was expecting based on the thread title.

FTR, I would not be offended if someone asked whether I were gay, straight, or bi. So I would suggest you just ask him.

11

Are you sure you aren’t? :wink:

12

I will also second this strategy. It’s non-intrusive about his lifestyle, while still getting you the information you would need to fufill his request for you to help him find somone to go out with.

13

Thanks for all the advice, guys. I met my friend for coffee yesterday and just asked him. He looked a little surprised at first, but he did admit that he’s gay. He also asked me how I knew. I just said that, after trying to talk to him about his relationships, and never getting any indication about what type of person he was going out with, I just wondered. He reminded me of a friend of mine who came out last year, and I mentioned that, too. He then asked me if I thought anyone at the office knew, and I said no, I don’t think they do. His office is comprised primarily of men who are rarely there. They’re all real estate brokers, so they’re usually out showing industrial properties and schmoozing their clients to make a sale. They rarely pay attention to the people who work for them (they’re all real dickheads and consider most of the office staff hired help and beneath their notice, but that’s beside the point).

Anyway, he said he was glad I asked because after he asked me to set him up with someone he wasn’t sure I knew about his orientation and he wasn’t sure he wanted to tell me, so he was kind of worried I’d set him up with a girl. Anyway, I asked him about my other friend, the one I think he’d like to meet, and he said he’d love to meet him. I’ve talked to the other guy, too, and gave them each other’s numbers. So, hopefully they’ll meet. My friend is kind of shy, so my other friend will probably have to make the first move.

When I asked him how on earth he expected me to set him up without knowing for sure that he’s gay, he basically said that he forgot for a moment that I was one of his friends who didn’t know. I was pretty flattered because he’s not someone who feels really comfortable with a whole lot of people. Anyway, I’m hoping this works out for him. He’s soooo nice, and he definitely deserves to be happy. Then again, I don’t know that many people who don’t deserve to be happy, but that’s one of those other things that’s beside the point.

Sorry for the long rambling post - I didn’t get much sleep last night, and I’m catching up on my coffee quota, but haven’t quite hit the mark. :smiley: