1. Get permission first. Never presume a pal is unhappy just because she isn’t attached at the moment. “People in relationships sometimes think anyone not in one needs to be in one,” Dr. Locker says. So check that your friend actually wants your matchmaking help. “Say, ‘I have someone I think you’d like to meet.’ If she’s divorced, don’t ask why she isn’t dating or say she should meet this person. Just ask if she’s ready,” suggests Dr. Locker. And never ambush her with an impromptu setup. “It’s offensive and alienating,” she adds.
2. Choose the right mate. So your friend’s on board. Still, you shouldn’t set up two people just because they’re both single, says Fay Goldman, founder of Meaningful Connections in New York City. “Think about their sense of humor, their relationship goals and their professional status,” she recommends. “If she’s career-driven, someone who isn’t might not be a good match. If she wants to remarry, a newly divorced guy who’s playing the field isn’t the right fit.” Adds Dr. Locker, “While you can’t account for chemistry between two people, the only real question for you is, ‘Would this person like this person?’ If there are no romantic sparks, at least they might enjoy each other as friends.”
3. Don’t be afraid to match your friend with a younger man. Goldman says many divorced guys in their 30s and 40s date older women because they don’t want to disappoint a partner of the same age or younger who wants children. And your friend might be into dating a younger man, too. “Often, women in their 40s and 50s are on the same plane with younger guys,” Goldman points out. “They’re fitter than men their own age and they’re financially independent and together.”
4. Skip sales pitches. “Smart” and “good-looking” are very subjective descriptions. “If you’re well-intentioned, no ‘selling’ should be necessary,” says Carol Morgan, founder of Carol Morgan Traditional Matchmaking in Boca Raton, FL. “Avoid those overused adjectives and concentrate on the individual’s character, integrity and core values.” If there’s a potential dealbreaker? “You can share with her, ‘I don’t care if he’s X, Y and Z, but you might,'” Dr. Locker suggests. “Full disclosure is best. Show her a photo if you have one.”
5. Be clear about how you know him. It’s important to be upfront about how you met and how well you know the man to avoid any misunderstandings and damage to the friendship, Dr. Locker says. “For example, say, ‘He’s a nice guy I knew in college, and we reconnected on Facebook recently. I think you’d like him.'” And if you don’t know the match too well, be honest. “And explain to the guy what your friend means to you,” Dr. Locker adds. The match needs to know how much you care about the person with whom you’re setting him up.
6. Pick the right venue. If you’re arranging their first meeting, avoid loud locales, Goldman says. “The most important thing: They need to talk,” she says, so no movie theaters. But also, “No long dinners at someone’s home. Three hours stuck with someone can get awkward,” she adds. A casual party or a drinks outing with friends is an easy, relaxed way to meet without the stress of extended one-on-one conversation.
7. Manage your expectations. Dreaming of the speech you’ll give at their wedding? Rein it in, Dr. Locker advises. Expressing excitement puts unnecessary pressure on them, she says. Don’t say, “I know you’ll love each other,” or after they meet, “Isn’t he amazing?” They’re meeting because they might enjoy each other-not to please you. Say, “Meet and see what happens,” and after they do, ask questions like, “What did you think of him?”
8. Only interfere if there’s confusion after the first date. She thinks he’s not into it, but he told you he is. “Nervousness can make people read a situation differently than it really is,” Goldman says. “Tell your friend he’s interested only if he expressly told you so.” That’s where interference stops. It’s up to them to pursue another meeting. Coercing either to meet again could harm your friendship and put them in an uncomfortable situation.
9. If disaster strikes, don’t take it personally. Everything that happens during the date is out of your control. “If you refer a friend to a dentist you’ve been going to forever, and it goes haywire, you can’t be responsible for what happens,” Dr. Locker says. Don’t blame yourself if either has negative reactions to each other. If she’s upset with you, remind the friend your intentions were good and chemistry is unpredictable, Dr. Locker adds. If there’s someone else you think she may like, see if she’s willing to go for another setup.
10. Be sure you’d be happy for them if it works out. “The only reason you should set up two people is because you think they’d like each other,” Dr. Locker says. “If there’s any other motivation,” say, you like the guy and want to be closer with him, “it could ruin the friendship.” Before you act, assess your feelings for him. If he’s someone you used to date, you can set him up with the friend, Dr. Locker says. “Just tell her, ‘This wasn’t my cup of tea, but he might be yours.'” Once you sort out your feelings about the match, ask yourself if you and the friendship can weather any jealousy over your friend’s new relationship. Only you can answer that.