It can be so tempting to set friends up. If you love two people, then they must love each other, right? If they both love you then they must enjoy many of the same character traits and hobbies. What could possibly go wrong? And everyone wants that credit of setting up a couple that works out. You have dreams of giving that toast at their wedding, “Hi. I made this happen.” Well, you’d be a bit more humble than that. In actuality, that toast is probably never happening because that wedding is probably never happening because, in my experience, setting up friends usually doesn’t go well. The closer the friends are to you, the worse the aftermath is. It’s nice that you want to hook up your friends but, if for a second, you think about it selfishly, you may realize how setting up two friends can backfire for you.
They may find the setup insulting
There’s nothing like a setup that shows people how others perceive them. If you set up one friend with someone who she thinks is far less attractive than she is, she could be insulted. Or, if he’s not conventionally successful, your other friend may think you don’t think she’s successful. You were trying to do a good deed, and now you have a friend who is offended.