Please tell me not to play matchmaker

[veryfluffy]

I am having to hold myself back, and I know that I should NOT get involved. Playing matchmaker is a minefield of etiquette nightmares, not to mention a sure way to doom friendships. But what do you do when you know two people, both of whom you know are interested in finding Someone, who would be  perfect for each other?

I always think that deliberately matchmaking in the way of "I know someone who would be perfect for you" is a terrible idea -- even if they do click, if it does go wrong later you risk losing both friendships. In this case, though, I don't know either of them all that well, ie they both seem like wonderful people but I don't know if either has strange habits, weird personal baggage, or a recent acquittal on a technicality on a charge of axe-murdering.

Both the people in question are in their late 40s, and both came out of rather difficult divorces a few years ago. Both are what I would consider average-to-pleasant looking and very ordinary, ie in a good way. But having got to know both these people, it suddenly struck me how they would be a good match.

There is no way these people are going to meet. The female concerned is someone in my village that I chat with frequently and meet up with to walk our dogs. The male is a customer of mine, from the town about 10 miles away, but we have chatted quite a bit and I know quite a lot about his life and interests. Unfortunately, he's not a "friend" or someone I meet socially -- otherwise it would be very easy to engineer a meeting to let them get to know each other.

Please tell me to mind my own business, and just hope they both join the same online dating agency.

[TurtleDove]

I don't know either of them all that well

Don't play matchmaker. 

[Outdoor Girl]

Please tell me to mind my own business, and just hope they both join the same online dating agency.

Encourage them both (separately) to join a particular dating agency?   

Yeah, myob is the way to go here.  If you knew them both casually and could invite them both to a party at your house where there were several other people also invited, fine.  But since this isn't possible, myob.

[Amara]

Could you have a small dinner party or a casual barbecue and invite both of them along with a few other interesting guests? No pressure, no matchmaking, just an opportunity.

[MrTango]

Don't play Matchmaker (said per your request)...

Instead, the next time you have reason to host a social event, invite these two people (along with other friends).

Introduce them to each other as you might introduce anyone at your event who doesn't know the others there.

If they end up together: Great. They'll always remember that they met at your event.  If they don't, it's no big deal.

[veryfluffy]

I would love invite them both to the same event -- except, as I mentioned in the OP, I don't know the chap (call him "Adam") socially, only through business. We always have very pleasant, extended conversations when he comes in, but that is only once or twice a year, plus a few phone conversations. It just wouldn't seem natural at this stage to try to invite him to something. I'm not really sure how to determine when or if it is appropriate to develop a business relationship into a friendship, either. Besides which, I just never have parties anyway.

If I was going to matchmake, what I would do is to mention Adam to the girl ("Eve"), and suggest she just happens to be at my place next time Adam comes in -- he has an appointment next week. There is a bit of waiting around involved, so it would be perfectly natural for them to chat for a few minutes. If she is interested, I would email him and say, this is a bit high-school, but my friend was wondering if he was single, and did he want to contact her. 

And that is where I think it would probably not be a good idea. Except it seems a shame not to give nice people a chance to meet each other.

[JennJenn68]

Okay, then don't do it.  As requested. 

But are you going to forgo this advice?  Oh, be real, nobody takes advice unless it's precisely what they wanted to hear.  Do whatever you feel is necessary.

[sweetonsno]

I am having to hold myself back, and I know that I should NOT get involved. Playing matchmaker is a minefield of etiquette nightmares, not to mention a sure way to doom friendships. But what do you do when you know two people, both of whom you know are interested in finding Someone, who would be  perfect for each other?

I always think that deliberately matchmaking in the way of "I know someone who would be perfect for you" is a terrible idea -- even if they do click, if it does go wrong later you risk losing both friendships. In this case, though, I don't know either of them all that well, ie they both seem like wonderful people but I don't know if either has strange habits, weird personal baggage, or a recent acquittal on a technicality on a charge of axe-murdering.

Both the people in question are in their late 40s, and both came out of rather difficult divorces a few years ago. Both are what I would consider average-to-pleasant looking and very ordinary, ie in a good way. But having got to know both these people, it suddenly struck me how they would be a good match.

There is no way these people are going to meet. The female concerned is someone in my village that I chat with frequently and meet up with to walk our dogs. The male is a customer of mine, from the town about 10 miles away, but we have chatted quite a bit and I know quite a lot about his life and interests. Unfortunately, he's not a "friend" or someone I meet socially -- otherwise it would be very easy to engineer a meeting to let them get to know each other.

Please tell me to mind my own business, and just hope they both join the same online dating agency.

I think it would be a really bad idea to matchmake in this situation. It's not clear to me why you think they'd be perfect for each other, beyond the fact that they are in the same "league," both divorced, both looking, and have mentioned having a few of the same interests. You aren't super-close to either of them, so chances are that you don't really know them well enough to know what they want/need in a match. You also can't tell whether or not there would be any sort of chemistry.

It's one thing if one or both of them have asked if you if you have any single friends. It's quite another to volunteer them for one another (which is essentially what you would have to do if you aren't close with either).

I agree with the posters who say that if you were closer to them, you would be able to invite them both to a party, without stating explicitly that you are trying to connect them. However, it would seem strange to invite them to a party barely knowing them. I also wonder if you might run into problems deepening your relationship with a customer. I'm not sure if crossing the professional line would be a good idea.

I think that if they mention that they are still looking, you could recommend a dating service (online, matchmaking, speed dating, etc). If you just so happen to recommend the same one and they wound up connecting that way, well, you've accomplished your goal without jeopardizing your personal and business relationships.

[Moray]

I've always found that if there's a small, niggling voice in the back of my head saying "Don't do it!", it's a good idea to listen.

[Petticoats]

You could always just ask each of them up front if they would be interested in having you set them up with someone. They might say, "Ugh, no," and then you wouldn't have to worry about it.

[Twik]

I've always found that if there's a small, niggling voice in the back of my head saying "Don't do it!", it's a good idea to listen.

I think this should be placed on billboards and bus ads over the entire country.

[nalapuppy]

You could always just ask each of them up front if they would be interested in having you set them up with someone. They might say, "Ugh, no," and then you wouldn't have to worry about it.

This is what I was thinking too.

[NutMeg]

If you don't even know them well enough to invite them over to your house, then you don't know them well enough to be playing matchmaker.

[Isometric]

Ahh, I know how tempting it is! But it can get intrusive and embarrassing for the people involved.

If the situation came up, I think it's fine to introduce them - there's absolutely nothing wrong with that. They may not get along at all, be soul mates or something in between. When I say introduce, I don't mean "Sue, here's Barry, *nudge nudge wink wink*" by the way 

Is it possible for your female friend to meet you for lunch when you know the male is coming in?

[veryfluffy]

OP here.
I took the general advice consensus and left things alone for now. I suspect the situation, or something similar, might come up again, and I thought I'd better give a bit more detail.

Eve is someone I see fairly frequently, as we walk our dogs on similar schedules. I would consider her a friend, even though I don't even know her surname. She's been to my house, I know a lot about her life and interests, and I get along with her really well. But since I have never met anyone in her family, and I have only known her for a couple of years, I would not claim to know her well. So, for all I know, she is a crack addict, ex-hooker, or professional shoplifter...things she wouldn't necessarily mention to a casual friend.

Similarly, I have known Adam for around 4 or 5 years, but really only as a chatty and friendly customer, so he again I know quite a bit about his work history, holidays, and views about a lot of things. But I don't know if he has a gambling habit, convictions for GBH, or a fetish for smelly sneakers.

The trouble when you get to your 40s is that it isn't all that easy to meet potential partners, so it just seems like a nice thing to do to help out a tiny bit. But I would never do anything more than just introduce people to each other. This would be much easier if both Adam and Eve were purely social contacts -- if, for instance, Adam was another local dog-walker, it would be a doddle.

Even if I did have parties, which I don't really, Adam wouldn't be someone who would normally be invited, even though he's someone I could imagine becoming friends with. From an etiquette POV, I should probably start a new thread in the Work folder, about if and how it is acceptable to cultivate a more personal friendship with a business contact.