When Your Date Meets Your Pals

Is it time to bring your date into the fold of your friends? Here’s how to make the experience less stressful—and even enjoyable!—for everyone.

By Caroline Stanley

ou and your new sweetie are crazy in love, and now it’s time to let your friends get to know the object of your affections. While the journey past a gauntlet of friends can be a bit awkward, it doesn’t have to be stressful. We’ve diagnosed the most common roadblocks to camaraderie and provided tips for making the experience honestly enjoyable for all.

Meet-the-friends fear #1: Your pals will “know” your date
“The gay community is a lot smaller than the straight one, so whenever I start seeing someone, the chances are always good that one of my friends
It can feel weird to know these two have a past.
has dated him,” explains Steve, 38, from Ohio. Steve’s not alone in this situation — and it’s more likely to be a concern if you’re dating in a small town.

Buddy fear-buster: Dating expert Jill Hankoff, owner of the Gay Millionaires Club, agrees that friend-date overlaps are common. “When you discover one, politely acknowledge the situation and quickly move on,” she says. A remark like “Whoa — small world. Let’s not let that make things awkward for us” will get the job done. You’ll wow your date with your maturity (vs. giving him a jealous third-degree) and put your friend at ease (he needs to know he’s not going to get drama from you later). It can feel weird to know the two have a past, but remember, they didn’t work out for a reason, and you and your new love are moving along just fine.

Meet-the-friends fear #2: Your buds won’t like him
It’s the basic high school insecurity that your date won’t be cool enough. If you’re truly fearful about what your friends will think, that self-consciousness is likely coming from you. “If I’m insecure about a guy, I’ll keep him away from my friends,” says Brian, 26, from Boston. “You know your friends will be honest with you, so the question is, are you ready to hear about the negative things they’ll say, especially if you’ve been trying to overlook them?”

Buddy fear-buster: Before introducing yourselves to friends as a couple, Hankoff recommends making sure you’re comfortable with how you both act in groups (in front of your pals is no time to discover an embarrassing penchant for rugby chants). Then, just relax. “Friends are supposed to have your best interests at heart,” says Hankoff. “If they’re mean-spirited about your date, it says more about them than it does your date.”

Meet-the-friends fear #3: Your date will like-like your friends
“A group of us went out recently, including my friend Seth and his new boyfriend whom he’d been dating for a month,” says Brandon, 27, from Santa Cruz. “At dinner, the boyfriend really hit it off with another of our friends and even asked for his number!” Sounds so The OC, but it
“I never know what drunken horror story they’ll decide to tell him.”
happens. “I worry when I bring a new attractive guy to meet my friends, who are attractive guys, because sparks could fly,” says Josh, 25, from Wilmington, NC. This assumption of betrayal isn’t shocking to Hankoff. “Don’t bring your date to the candy store if you’re still trying to prove that you’re the sweetest thing there.”

Buddy fear-buster: Hankoff suggests waiting until things are serious before you introduce your amore, and making it clear that you’re bringing him as a boyfriend rather than adding a free agent to the mix. “Introducing long-term relationship material should signal a hands-off situation to the group,” says Hankoff. “If you’re just showing off your new cute fling to your friends, they might view him as fair game!”

Meet-the-friends fear #4: Your pals will embarrass you
When you’re first dating a new guy, you’re only showing him the parts of you that you want him to see. When he meets your friends, he gets access to all the not-so-pretty facts about your life before him. “I’m always reluctant to bring my new guy around my two best friends whom I’ve known since college. I never know what drunken horror story they’ll decide to tell him,” says Alan, 26, from New York City. Whether it’s a skeevy girlfriend from your pre-out days or that you got fired from your last job, there’s plenty that you might not want shared.

Buddy fear-buster: You can ask your friends to keep personal stuff off-limits for a while or just request that they avoid specific topics, like any that involve getting drunk and stupid or a particular ex he doesn’t know about yet. “But don’t take yourself too seriously,” says Hankoff. “Good friends know which stories are cute and which are just embarrassing — they won’t try to cross that line. If you’re surrounded by people who get off on making you look bad and potentially sabotaging your new relationship, it’s time to look for new friends.”

Caroline Stanley is a writer based in New York. Her work has appeared in CosmoGIRL!, Ladies’ Home Journal and Harper’s Bazaar.
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