How To Date Multiple People At Once Stress-Free And Have Fun Doing It

While lots of people are looking for monogamous relationships, maybe you’re not one of them. You want to see what’s out there, play the field a bit, and just keep things footloose and fancy-free. There’s nothing wrong with that! If you want to date multiple people and keep it a stress-free and fun experience, it’s easier than you think. Just follow these rules.

  1. Keep it all above-board and lead with honesty. If you want to date multiple people, each and every one of those people need to know about it. I’m not saying you should be sharing the nitty-gritty details of each of those relationships with the other people, but they deserve the right to know that they’re not the only one in your life. Always be upfront about what you’re up to and where you stand and as long as you’re all on the same page, you’re good to go.
  2. Don’t overbook or double book yourself. Be smart about this. Just because you have the freedom to date around doesn’t mean you need to overdo it. Plan a few dates a week, fine, but don’t have a date with someone new every single night of the week. Oh, and definitely don’t book multiple dates on the same night. That’s just not a good look. You’ve got time! Take it.
  3. Make sure you’re practicing safe sex. Dating multiple people means potentially sleeping with multiple people, and that’s cool. Get yours! Just make sure you’re doing it safely by using condoms, dental dams, and potentially birth control if you’re someone who could conceive and don’t want to. This will not just keep you safe but your partners too, and this is paramount.
  4. Avoid guys (and girls!) who are looking for serious relationships. If you’re dating someone who says they’re totally cool with you dating multiple people and keeping it casual but you know they’re also actually looking for something serious, cut your losses now because this will not end well. They’ll likely end up lashing out in anger when they realize you’re not going to suddenly go monogamous with them or they’ll end up with a broken heart, potentially both. You’re better off with people who are looking for the same laidback arrangement you are.
  5. Don’t try to act like anyone’s girlfriend. If you’re seeing five people but you start trying to play the girlfriend role rather than the casual date role, this is going to spell trouble. The whole reason you’re dating multiple people is that you don’t want to be anyone’s girlfriend, so what are you even doing? Don’t start running errands for anyone, being their #1 support system, or any other girlfriend tasks. It will not end well, I promise.
  6. Don’t feel guilty. At the end of the day, as long as you’re being honest about dating multiple people, you really have nothing to feel guilty about. Get out there and enjoy yourself – that’s what life is all about!
Jennifer Still is a writer and editor with more than 10 years of experience. The managing editor of Bolde, she has bylines in Vanity Fair, Business Insider, The New York Times, Glamour, Bon Appetit, and many more. You can follow her on Twitter @jenniferlstill