The DOs and DON’Ts of Dating More Than One Guy at a Time

“I was previously married for about six years and didn't really take the time to consider what I wanted out of a relationship or marriage,” says Megan, 27. “Now with dating more than one guy, I have been able to look at what each of them would add to my life and not feel pressured about one person. I can stay more objective until I make a decision about which situation and person better suits me, and vice versa.”

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Admit it: You know in your gut when you’re stringing a guy along. “It’s nice to feel wanted by more than one person, but you can’t let it continue if you’re not interested,” says Tova, 22.

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Learn from 24-year-old Dani’s dating mistake: “In my most recent relationship with a guy, we were very up front and honest about dating others, so much so that we talked with each other about our other dates,” she says. “That's where things started to get messy. I realized that although I was OK with the thought of him dating other women, I wasn't actually OK with hearing about it. That brought on unwanted jealousy.”

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Dating multiple men makes for a very high probability of getting busted, says Becky, 29. “Last St. Patrick’s Day I went to happy hour in the afternoon with one guy I was dating, and then I made an excuse and met up with my other guy. When I was walking to the bar, my afternoon date drove past and saw me with the other guy. He stopped and called me out on it, and I ended up losing both guys.”

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The risk of getting caught, however, can be part of the excitement of dating more than one guy. “I think I was so caught up in the ‘game’ of it all that being with just one guy almost seemed too monotonous for me,” says Becky. “Whenever I really liked a guy and would date just him, it wouldn’t seem like enough. It’s now created a fantasy land that probably doesn’t exist, but I hold on to the hope that somebody out there has it all.”

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Knowing why you’re playing the field can help you keep things in perspective. Forty-one-year-old Michelle made it a point to date more than one man after her divorce. “I didn't want to get attached to one person and risk getting hurt on top of the hurt I was already dealing with, or risk someone keeping me from leaving,” she says. “When one of the guys I was dating decided he didn't want to date me anymore, or there was something about him that I didn't like, it was easy to let him go.”

Just because you’re content with the way things are doesn’t mean your multiple men are. Make a point to touch base periodically. “I’m dating two guys right now, and I'm trying to let things sift out on their own while keeping a degree of neutrality,” says Megan. “But I try to progress things a bit by asking questions such as ‘To you, what is going on between us?’”

This advice sounds like common sense but can be surprisingly difficult when you’re in the moment. “I remember one guy I dated that I really liked and felt we had a lot in common, but my lack of full interest in him ran him off,” says Michelle. “In the end, what I really want is to be with that special someone and have a committed, monogamous relationship.”

When you have multiple people vying for your affection, it can be easy to pit them against one another until you determine a winner. “I thought I could wait to see which guy would step up, but every guy is different,” says Tova. “How can you compare apples and oranges?”

“Dating around can help you figure out what you’re looking for in a relationship, but don’t settle on one guy just to settle,” says Tova. “I strung along three guys for too long, until I finally realized I didn’t have to date any of them—I could choose to be single.”