With Valentine's Day on the horizon, this is an appropriate time to offer a few words of advice. I know that romance readers and writers tend to be a wee bit, well, romantic, and therefore they want everyone they know to find true love. That desire may be enough to make you want to play matchmaker with every single person you know. As a public service to single people everywhere, I have some words of advice for you:
1. Think about why you're matching people up. "They're both single and breathing!" is not good enough, and the fact that you love both of them doesn't necessarily mean they'll love each other. Can you imagine these two people having a conversation? What would they talk about? Do you know what they're looking for in a romantic partner? How well does that match the other person you want to set them up with?
2. Avoid mercy set ups. If your friend is a great gal who's beautiful, nice and friendly, that doesn't mean you should set her up with the guy who needs a confidence boost just because you know she's too nice to shoot him down. (I suppose it could work the other way around, but I haven't seen too many cases of a super-great, gorgeous guy being expected to ask out a loser girl just to make her feel better about herself.) If she's that great, doesn't she also deserve a great guy? And besides, there are limits to mercy, so if she does give this guy a chance and then realizes he's not for her, he's been set up to be hurt even more.
3. Avoid direct, obvious set-ups. That will help you prevent any problems stemming from the above guidelines. There's nothing more awkward than that initial introduction after you've been told all about this person you're meeting, and it turns out he's not at all what you expected -- or you can see on his face that you're not at all what he expected. Actually, I take that back. A blind date with that scenario is worse. Even worse is when you're so not interested and he is. Worst of all is when you're very interested, and he so isn't, and makes it clear. A better idea is to plan a party or other gathering and invite the people you want to set up -- but don't tell them about the set-up. Introduce them like you would any other guests who haven't previously met. If they're as right for each other as you think, they'll figure it out and go from there. If they aren't, then there's no harm done because neither will have high hopes to dash and they won't feel like they're performing monkeys being asked to dance for your amusement.
4. Be careful about your involvement in the follow-up. If you act like you're too invested in this relationship you've helped start, you make things very difficult on your friends. Not only do they have to factor each other's feelings into what happens next, but they may feel like they have to consider you, as well. If things don't work out, or if one of them rejects the other, they may be afraid you'll think they're also rejecting you. The closer the person you've set them up with is to you, the more difficult it becomes. Random coworker or bowling league buddy is one thing, but siblings, best friends or sons/daughters is a lot more difficult. Handle this the wrong way, and you may find your friend avoiding you for fear you'll be mad at her for rejecting your loved one.
Hopefully, if you've handled the set-up in a subtle way, they'll get each other's contact information. If they don't and get in touch with you to try to find out how to reach the other person, make sure that person wants to give it out. Don't try to create a guilt trip by talking about how much that poor guy needs a great girl or how much you want to see him happy. The relationship is about them, not about you.
So, now that you've got the guidelines in place, go out and spread love around. And if you know a great guy between about 35 and 45, invite me to a party where he'll be.