You know the perfect person for your good friend, and you're dying to set them up. Maybe both of them really love comic books or Wyclef, are great artists, or have the same silly sense of humor. "If it works out, they'll both feel happy — as well as grateful to you," says Carol Weston, author of Girltalk and For Girls Only.

However, matchmaking can sometimes be tricky. "Pushing people together is a terrible idea, and trying to talk one friend into caring about another can backfire for all," says Weston.

That's exactly what happened to Buck when he set up two of his friends. "I thought Monica and Janelle [names changed] would be perfect for each other," he says. Monica fell hard for Janelle, but unfortunately, Janelle wasn't ready for a serious relationship. "Janelle liked Monica as a friend and didn't want to hurt her — but eventually, she had to," explains Buck. The matchmaking experience was messy and painful for everyone involved.

Matchmaking 101

Are you thinking of setting up two of your friends?

Before you make a matchmaking move, improve your chances of success by asking yourself the following questions about your friends:

  1. Are they available? Tara's friends set her up with a nice guy. The only problem was Tara was still hoping to get back with her ex-boyfriend. Needless to say, the matchmaking attempt just didn't work out.

  2. Do they want to get matched up? As Buck found out, it's important for both friends to be on the same page about what kind of relationship they want. If one friend is looking for someone to date casually (like Janelle) and the other friend is looking for a serious, long-term girlfriend (like Monica), things can get awkward and people's feelings can get hurt.

  3. Do they match? Although sometimes opposites do attract, it's helpful for people to have compatible personalities. Someone who's shy and into quiet conversations, for example, may have a hard time hitting it off with a super-outgoing, life-of-the-party type. Common interests are also key — it can give your friends something to talk about or do together when they're first getting to know each other.

When it comes to your motivation for matchmaking, consider the following:

  1. Are you doing this for the right reasons? No fair setting up your buddies just because you're in the mood to double-date. Another no-no: you secretly lust for the person you're hooking your friend up with. Your goal should be making your buddies happy ... right?

  2. Are you communicating? Tell your friends a little bit about each other before they meet up. Clue them in on what they've got in common, so they'll have some good conversation starters.

  3. Are you being honest? Tell the truth about the people you're setting up. Avoid getting carried away with your enthusiasm and "overselling" your friends — it can lead to disappointment.

  4. Are you letting go? Once you've gotten your friends together initially, it's time to let the relationship run its own course. Don't carry messages back and forth between your friends, push for a second date, or take sides in disagreements.

Finally, don't get over-invested in your matchmaking endeavor. If the relationship doesn't work out, don't take it personally. You can help kick-start a relationship, but it's up to your friends to keep it running smoothly.