How to Set Up Your Friends Without Making It Awkward for Everyone

You’re the first person any of your pals calls after a bad day at work. You never forget a birthday, and sometimes you even send a card for no reason at all. You’re on a first-name basis with your BFF’s mom, and you feel pretty confident that you could successfully order brunch for most of your friends at any local restaurant. But you’re ready to take your gold star friendship status to a brand new level by helping all of your single friends find their next great romance. But setting up friends isn’t for the faint of heart — after all, you don’t want to risk the friendship! There are, however, ways to organize dates for the people in your circle without damaging your relationships with them, and we’ve asked the experts for their tips on how to do just that. Keep reading for seven suggestions that will help you make potential love connections without throwing your social circle into total chaos.

1. Have a good reason! Your friends aren’t destined for each other simply because they both happen to be single — and setting them up for that reason alone has the potential to offend them. “Think about why they would make a great couple,” suggests relationship expert and mental health writer Emily Mendez. “Don’t set them up unless they have things in common.” This might seem obvious, but if you’re excited about the possibility of your single pals hitting it off, you might get carried away and forget to really consider how realistic the relationship might be.

2. Don’t overcomplicate the situation. “If you’re setting people up, set them up!” says Nathan John, founder of UK matchmaking service You Should Meet. “Don’t arrange an intricate set of meetings at various social events before the actual introduction.” Assuming both parties trust you to set them up, go ahead and set the date for the two to meet. A more complicated strategy might confuse the issue or make your friends feel like they’re being put on the spot at other events.

3. Don’t set up friends with a dramatic breakup history. Breakups are never easy, but there are people who are more prone to dramatic splits than others. These people may not be the best candidates for a friendly setup, particularly if you’re nervous about the future consequences of making such a match. “Some people have a pattern of volatility in their relationships,” Match Made in NOLA founder Ann Parnes notes. “If one of your friends matches that description, it is probably best not to introduce them to another friend.”

4. Keep things low-key. Once you’ve committed to making the match, you can avoid putting unnecessary pressure on both people (and on yourself!) by ensuring that the introduction is casual and the first date is light. Make the connection at a laid-back event like a birthday party — and only once, per John’s advice — and suggest that the date happen at a fun, not-too-formal setting like a trendy casual restaurant or miniature golf course. “Even if the two don’t end up pursuing a relationship, your friends will appreciate your efforts if you went about it in a nice way,” encourages Maple Holistics wellness expert Caleb Backe.

5. Be realistic. Don’t oversell the situation to your friend. If you’re excited to set them up on a date, it’s entirely possible that you’ll exaggerate the odds that they’ll fall immediately head over heels with the person in question — and while that would obviously be ideal, it kind of sets everyone up for disappointment. LastFirst founder and CEO Emily Holmes Hahn recommends a healthy dose of realism as you prepare your pal for the date. “It’s better to leave a little mystery so that the couple will be pleasantly surprised upon meeting, rather than disappointed,” she tells us. “So much magic is involved in making a match, and if this is going to be the real thing, you need to allow that moment the couple locks eyes for the first time to be raw and not build up expectations too much.”

6. Make the match and walk away. If you’ve made what you think is a promising introduction and put the two parties in touch, it’s time to back off. Doing so will help ease any jitters you might have about the effects of a romantic setup on your friendship. “Sometimes, friends feel hesitant or weird about being set up, because they’re afraid you’re going to dig and ask about every little detail,” says DC-based Three Day Rule matchmaker Kat Haselkorn. “Give the relationship room to develop slowly and naturally.” If things are going well, we’re confident your friend will let you know! And if not, well, maybe it’s best you don’t talk about it.

7. Frame any feedback constructively. If you’ve heard from one friend that the other didn’t come off so well on the date, take a beat before you report back. They have a right to know what happened — especially if you think they might be waiting for a call back — but it’s easy to make someone feel attacked or criticized in situations like this. Rori Sassoon, owner of high-end matchmaking service Platinum Poire, recommends that you express it as constructive feedback. “Frame it so that it comes off that you are trying to help and not criticize,” she says. Who knows? Your friendly advice could be the key to your BFF totally crushing their next date, even if it’s not one that you’ve set up!

Have you ever set up a friend? Tweet us how it turned out @BritandCo!

(Photos via Getty)