Advise required: setting up friends

Miscellaneous and Personal Stuff I Must Share
1

So I went on a company dinner cruise last night. As my fella is currently 3000 miles away, I brought my sister as my date. Unexpectedly, my friend, we’ll call him Bob, actually showed up, too. Bob and I are pretty good work buddies. He and another coworker and I take two breaks a day and our lunches together. We are recognized as a clicque at work.

Bob and I actually went on one psuedo-date about three months ago. We discovered that we had a mutual friend, and the three of us went out for drinks. Mutual friend sneakily excused herself early, leaving Bob and I alone. He’s terribly cute, and more or less what I would be looking for, but he’s pretty neurotic, I work with him (that’s the BIG kicker) and I do have this sorta understanding with the boy who is 3000 miles away that when he gets home in 6 months, we’re gonna be a Thang. So while I like Bob a lot, the fact of the matter is that I’m in love with someone else, and I work with Bob, so I didn’t want to go there.

Which is good, because Bob and my sister TOTALLY hit it off last night. He apparently asked her out, and she told him she’d have to check with me first. I told her to go for it, and gave him her number.

Here’s the question: I know both of them VERY well. I know how Bob’s last couple relationships ended, and why. My sister and I are so much alike that it drives us both crazy. So obviously I know her very well. The question is: how do I not involve myself in this? I mean, I want them to hit it off, I want to be a good yenta, but I don’t want to get stuck in the middle. Especially since he’s a Nice Guy and she has a habit of letting Nice Guys fall madly in love with her before she realises she’s not interested. The adult part of me says “Don’t do ANYTHING. Don’t tell him to take it slowly with her and let her come to him, don’t tell her to not lead him on if it’s not there, you’re just putting yourself in the middle if it goes badly that way.”

I really don’t want him to get hurt, which is what she tends to do. I’ve never set two people up when I know BOTH of them so well. Usually it’s that I’m closer to one then the other. But I share 8 hours a day with one of them, and DNA with the other. Yikes.

Any advise on how to NOT get stuck in the middle?

2

the one thing i would say to be aware of is, if it doesn’t work out,
they will not want to be in the same room together which puts stress on your relationship with both of them (as in ‘who do you side with’)

still if it goes well, you are already great friends with the ‘partner’

so , basically i don’t know what my advice is!

3

Tell them both separately that you do not wish to be put in the middle. :smiley:

4

Tell them, seperately, that you don’t want to get stuck in the middle. That you’re walking a pretty thin line here and don’t dragged into any arguments OR petty disputes. Wish them the best of luck in this but otherwise you don’t want to be involved.

If either one comes to you with ANY details, just say you’re sorry but you aren’t getting involved with this.

Eh, good luck! This is going to be really sticky for you. I can just see my sister telling me odd prurient details about my co-worker - and everytime I’d look at the co-worker THAT would be the only thing I’d think about. “Hmm, feet… whodathunkit”

5

I know it sounds like an echo chamber in here, but DON’T get in the middle. It’s not only hard on you, but it can hurt their relationship, too, if instead of telling things to one another, they tell them to you as a conduit to the other person.

6

What they said.

Stick your fingers in your ears and chant “la la la” if one or the other tries to tell you something.