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7 tips for successfully dating more than one woman at a time

By / 06.11.12

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Dating more than one person at a time can be empowering and a lot of fun, but it can also be an good way to gauge what you really want in a long-term partner. It allows you to disengage from the blinders of settling prematurely, so when monogamy is ready for you, you’re ready for it. It’s about making the right choice that celebrates a mix of unromantic qualities like stability and compatibility with more immediate ones like passion. But it can be tough to juggle two or more uncommitted relationships at once. So, how do you achieve it while showing respect for everyone involved?

7 Don’t Volunteer the Wrong Information

Many women date more than one guy at the same time. But even if they aren’t, it doesn’t mean they’re interested in your dating details. So, what’s an example of the wrong info? Saying something like “You’re my top bitch” or “Sorry, I can’t. My Tuesdays are reserved for Kim” have the potential for disaster. Be discreet when it comes to your outside dating life.

6 Be Clear

Even though spelling out your situation outright is in bad taste, you can be clear and give the right expectations by letting women know about your dating tendencies. When it comes up in conversation, be up front. If commitment is so important to you that you’ll only give it to an important person who’s the right match, then hopefully she’ll understand. If she doesn’t, maybe she had poor experiences with similar arrangements in the past or is just a bit insecure.

5 Be Safe

Yeah, you definitely don’t want to get someone you’re seeing casually all preggers. That goes double if she seems like the type that would go “pregcognito” (secretly pregnant), not telling you about it. What about da’ butt, you say? While I’m fully aware that it’s not biologically viable to have an ass-baby (YET!), there are other things to watch out for; hint, hint, they rhyme with “Test These Trees.” You should always remember (especially while seeing multiple women) to wrap your tool, put on your jimmy hat, slap on the rubber, sheathe the sword, glove the fist and put on your crotch-catcher.

4 Remember to Evaluate

Sure, it can be a lot of fun to have more than one hook-up partner at a time, but it’s also important you use the opportunity to discover what you look for in a serious relationship. You may notice that certain qualities from each person align with your needs, while others don’t. This will give you a good framework for finding a single, single woman who has a good mix of those qualities.

3 Know How to Turn it into Something More Serious

If things are going well with someone you’re seeing and you want to take it to the next level, it’s best to gauge her attitude toward you and your current arrangement. If they seem to be in the ballpark of your feelings, then go for it. Just make sure you know how to break it off with anyone else you may be dating.

2 Know How to Break it off the Right Way

If you think that she isn’t the one, don’t ignore it. If her feelings toward you don’t seem strong, it may not require immediate action, or any action at all (until it’s time for one of you to move on). But, if there’s a big disconnect between how you feel about each other, it’s best to be honest. Let her know you enjoyed your time together and that because of all her good qualities she’ll find a great guy who is a better match for her.

1 Don’t Ask, Don’t Tell

If you’ve got the right to slut around, so does she and it’d be wrong to hold it against her or expect otherwise. After all, she’s a woman and she deserves to have a good time and make the right choice for herself as well. Don’t ask her details about her dating life and hopefully, you can expect the same from her. And if it’s meant to be, you’ll know.


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Jason Epstein
About Jason Epstein... Jason Epstein is a nationally published freelance writer living in the greater NYC area. He's known for his close friends/good conversations/playing bass/wind in the face/rocking out/reading up/holding it down/good times/turning on dimes/and sometimes trying to rhyme(s). He can be reached at his website and you can follow him on Twitter here.

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