Recently, Olivia Wilde brought her fiancé Jason Sudeikis to her old high school to show him around and let him meet the people who made up her experience there. And while it can be awesome to introduce your current guy to your old life for the first time, it can also bring up some seriously awkward moments—like, say, when he meets the ex who broke your teenage younger self’s heart. But with a little planning, it’s easy for both of you to have a blast. Just follow these four guidelines.[Tweet these tips!]

Know Your Title

Sounds obvious, but dating experts warn that a reunion-like environment is the worst place for “what are we, exactly?” misunderstandings to occur. Even if it’s a happy hour, make sure you and he are on the same page as far as how you guys will introduce each other. “Having the exclusivity conversation before you introduce him to friends as ‘your boyfriend’ is key, even if it’s uncomfortable,” says Tara Richter, author of 10 Rules to Survive the Dating Jungle.

Play His Wingman

Instead of simply introducing him to the entire group as “my boyfriend,” make an effort to show him off one-on-one with a brief detail he shares with each person he meets—i.e., let your wave-worshipping cousin know he just came back from a surf trip. The more connections he can make with your old friends, the less you’ll feel like you have to be by his side every second, reminds Richter.

Get a Little Handsy

Grab his hand when you’re introducing him to a former flame, or rub his thigh when the conversation rolls back to the epic nights out you and your old roommate used to have. Making sure you and he have body contact will subconsciously remind him how much you want to be with him, even if the conversation is about yesteryear, reminds Karla Moore, an Atlanta based dating coach and matchmaker.

Remember the “We” in Weekend

If the two of you are spending a weekend with your old pals or extended family, research cool stuff you can do alone together, whether it’s taking in a baseball game or checking out a new bistro in town, suggests Moore. And be honest about expectations: Do you want him by your side the whole time, or are you fine with him solo sightseeing while you and your girlfriends catch up over manis? An upfront conversation will help you avoid misunderstandings, Moore adds.

BDST: 1235 HRS, APR-29, 2014