Bold First Date Ideas That Could Make Or Break a Relationship

If these risky dates go well, it could mean a beautiful future

Doing something non-traditional on a first date is big risk — and potentially disastrous. That being said, making a bold choice for date #1 could also mean an unforgettable memory that brings you close from the get-go, thereby launching a potential relationship.

Feeling adventurous? Here are a few of our suggestions.

Skydiving

What better way to show your date your authentic self than careening toward the ground at 120 mph from 12,000 feet in the air while strapped to a dude who probably has a really unsettling nickname like “Pancake?” Don’t answer that, because sure, there are probably better ways, but skydiving is a quintessential thrill that you and your date will never forget. The only downside is getting some small talk in with your partner while that guy Pancake is strapped to your back. That guy should really think about getting a new nickname.

Play Paintball

While, admittedly, heading into the woods for an intense, simulated war game may not seem like a great idea for a first date, paintball provides a fun way for people to connect through working together and achieving a common goal. Paintball also provides a small whiff of danger, which according to most movies, is strong aphrodisiac. The downside is that maybe your date isn’t into running through the woods with a pressurized weapon trying to avoid getting hit with welt-inducing balls of paint, so it would be wise to not surprise your partner with this date, unless of course, you’re on the same team.

Museum Of Sex

The Museum Of Sex, or MoSex, is a New York City museum dedicated to the history and cultural significance of human sexuality, but don’t think for a moment this is some stuffy Smithsonian-type museum. Among MoSex’s most popular exhibits is “Jump For Joy,” a full scale moon bounce made entirely out of giant inflatable boobs.

A stroll through the Museum Of Sex’s 20,000 permanent artifacts and NSFW exhibits is a great way for your and your date to have a dialogue about your sexual preferences in a sex positive and empowering environment—just be sure that you and your date are comfortable before committing to a day of inflatable boob bouncing and staring at statues of skeletons boning. Also, make sure that your date knows that this is a real museum, otherwise “Want to go to the Museum Of Sex?” sounds like the creepiest pickup line in the world.

Fan Convention

If you and your date have a shared interest (read: obsession) in a specific fandom, a convention is a fun way to bond over your common geekiness. Most conventions contain a never ending sea of vendors and a packed schedule of panels so you can easily spend an entire day getting lost in nerdom. Since cosplay is a big part of the convention culture, you can show off your creative side by putting together a zany costume, or just go plain clothed and enjoy people watching. Conventions can be very loud and crowded and tend to be a bit…much. But if your date is as interested (read, again: obsessed) with the subject matter, it will definitely make for an interesting day.

Rocky Horror Picture Show

Over the last forty years, The Rocky Horror Picture Show has become a cult phenomenon and a right of passage for folks young and old who just want to let their freak flags fly. Everyone, at least once, should experience it live. Just beware that if you or your date’s first time you may have to get up on stage, bend over, and have the audience scream a certain word that starts with the letter “f” at you. Loud and sometimes overwhelming, The Rocky Horror Picture Show isn’t ideal for shyer folks, but if tossing rice and screaming at a movie screen sounds up your alley it’s an experience you won’t forget.

Meeting Your Parents

Somehow, of all the items on this list (including jumping out of an airplane), meeting mom and dad is the most terrifying. But, here’s the thing, if your relationship is going to work, you’re going to have to do it eventually, right? Introducing your date to your parents is a great way to show that you’re a family-oriented person and that you’re looking for a serious relationship instead of just a fling. It’s a risky move, but if your date is comfortable and ready for it, it could establish a great footing for a lasting relationship.

Sleep No More

Sleep No More is a New York City based performance that defies explanation. Spooky and unnerving, it’s theater meets haunted attraction channeled through Stanley Kubrick’s Eyes Wide Shut. The immersive experience—any immersive experience, for that matter—guarantees conversation fuel for future dates. But, if you’re not the type who enjoys spending three hours wandering around a creepy hotel as a group of actors silently perform an impressionistic version of MacBeth around you, maybe just stick to drinks.

Local Government Meeting

Local government meetings are long, dry, boring, and not exactly an aphrodisiac. They are, however, a way for you and your like-minded date to bond over your shared values and passion your community. As unsexy as a night at a town council meeting might sound, you can always head out for drinks afterwards to discuss the hot button issues of your community, like what the zoning requirements would be to bring an inflatable boob moon bounce to your municipality.

Written by Matt Schmid.

Make a bold first date move on OkCupid right now.