Online Dating: Six Tips for Family and Friends Playing Cupid for Newly Single

After his wife of 30 years died, Tom’s friends hated to see him grieving so deeply. So, almost immediately, they set him up with a woman who was trying to turn her life around after a series of relationship failures.

Tom was such a great guy, they just knew this was a happily-ever-after-story. He married her. Only, Tom wasn’t really done grieving his wife and the woman, who had major trust issues, made his life a living hell. Seven years later, he lost his home when he divorced her.

Do you know someone whose life is a sad story and just needs the right person to make all the bad things go away? People with more issues than Time Magazine don’t need a rescuer, they need a therapist. So, be a good friend and don’t set them up with someone you want to remain your friend.

Know thy friends. You can’t know in advance if sparks are going to fly. It’s OK if you set your friends up with someone with similar interests only to discover there’s no real chemistry. On the other hand, setting up a swinger with someone who’s into monogamy or a liberal pro-choice vegan with a conservative pro-life carnivore might just enrage your friends who could rightfully wonder if you really get them at all.

So, before setting someone up, think about their morals, values, hobbies, and lifestyle as well as their hopes and dreams. The most important quality matchmakers need to succeed is insight into their friend’s character and behavior. “‘Getting you’ is more important than absolute detail about what you’re seeking in a partner,” said Trish McDermott, former vice president of global communications for Match.com. Here are some tips to help as you play matchmaker for a newly divorced friend or family member.

1. Set your boundaries.

Decide if you will answer questions or pass on gossip and information about one friend to the other. Although it’s tempting to help friends this way, after the initial introduction, unless something comes up that your friend really needs to know, being an information conduit may give the impression that you can’t be trusted.

2. Be discreet.

It isn’t always necessary or even best to make the big announcement that you have someone you want them to meet. For some people, set ups feel more natural if you just create a number of opportunities for two people you think would be great together to be at the same events. Don’t take it personally. If the people you set up don’t think they’re a good fit, that’s OK. The best matchmakers detach from the outcomes and keep thinking of someone else who might make their friend happy.

3. Have fun.

We have a very natural interest in helping people make connection, especially romantic connections. So, make this fun for you. Get to know the other great people in your friend’s network and brag about him or her with a realistic balance. “Throw in something cute about some of their quirks such as she cries at every romantic movie I’ve ever taken her to,” said McDermott. However you do it, remember it’s about being authentic. By helping your friend not only will you expand your own circle of friends, you’ll also be much more likely to be perceived as an attractive person yourself because you are a person who cares about other’s happiness.