How To Date Multiple People & Not Feel Like A Jerk

Photo: Bob Du2019Amico/ABC.
If you're seeking a cautionary tale about what can go wrong when you're dating several people at once, just watch Bachelor in Paradise. The whole point of the show is to see what happens when you put a bunch of singles together and tell them to date, which is why it's so amazing and so awkward.
On last night's episode, the love triangles started to take form: Matt chose to go on a date with Christen, pissing off Jasmine, who had been consistently seeing Matt. Then, Dean said that he was "infatuated" with both Kristina and Danielle L. In the previews for the rest of the season, a very teary Dean weeps, "I think I'm just attracted to two people."
Despite how delicious the drama can be in Paradise, it is possible to date multiple people at the same time without explosions or hiccups like you see on the show. In fact, a 2014 study found that, although consensual non-monogamous relationships are often stigmatized, they're not any less stable or more unhealthy compared to monogamous ones.
All it takes for a non-monogamous relationship to work is adhering to three simple rules: Be honest about your intentions, communicate when they change, and don't beat yourself up, according to Jessica O'Reilly, PhD, a sexologist and host of the podcast Sex With Dr. Jess. "Some people are more honest about their intentions from the onset, and they therefore have happier relationships — regardless of whether they date one or multiple people at a time," Dr. O'Reilly says.
Some people might just be better at dating many people at once. "We do have some preliminary data to suggest that certain personality types are more likely to seek consensual non-monogamy," Dr. O'Reilly says. For example, people who tend to score high in openness are more likely to date multiple partners. "Other research suggest that sexual personalities may also play a role." There's some evidence that people who have positive attitudes toward sex, and enjoy trying new sexual activities, might fare better in consensual non-monogamous friends-with-benefits relationships, according to Justin Lehmiller, PhD, director of the social psychology program at Ball State University and author of the blog Sex and Psychology.
If that's not you, all is not lost. "You can custom-design your dating and relationship life according to whatever suits you and the people you're dating," Dr. O'Reilly says. In general, talking about your rules, boundaries, needs, insecurities, desires, and fears is the first step. And probably the second-through-fourth steps, too. "When more people are involved, you'll need to have more conversations," she says.
And once you have discussed what you want from your setup, you still have to check in to see how your partner is faring, and whether or not they're still satisfied with the arrangement, Dr. O'Reilly says. When you are juggling a few loose relationships, there's a tendency to just brush over the deep topics, and keep the conversations light — but that's not a very good strategy if you want to have sustainable relationships. "It's important that your communication is honest and includes expressions of vulnerability," she says.
In addition to the emotional gymnastics required to juggle several dating partners, there are also some logistical challenges. For example, how will you introduce someone you're dating to other people? And what are you going to do when you run into one of your partners while out with another? "You may want to consider practical rules and guidelines," Dr. O'Reilly says. This might be a bit much, but Meredith Golden, a matchmaker and dating coach who specializes in online dating, suggests making a spreadsheet of everyone you're dating, including the number of dates you've been on. Or, perhaps a note in your phone would suffice.
If you identify with Dean's struggles, and feel bad about the fact that you're seeing a few people, then it's important to remember that you're allowed to date however you want. "You shouldn't feel guilty or ashamed of your natural desires, as long as your behavior reflects a genuine effort to be honest and treat others well," Dr. O'Reilly says.

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