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How to Respectfully & Successfully Date More Than One Woman at a Time

I’ve never seen anything like it. There is a steady stream of hot lesbians marching through my door, moon-faced and glassy-eyed, happily dating the same woman. That woman is my roommate, a buoyant Dutch personal trainer who joyously skips through life as I shuffle through existence. She’s not a player or polyamorous; she’s just dating.

Remember dating? In our rush to simultaneously shed and cook up obscure new labels, we’ve forgotten about dating. Dating: seeing more than one person at a time with mutual respect, physical attraction, and no long term commitment. Dating dating. I asked how she balanced dating several gorgeous, smart, interesting women at once, and together we came up with 10 simple tips for dating around with poise and minimal drama.

Now you just have to find more than one girl who wants to date you. That was always the part I had trouble with.

No lie, no lie, no lie. You need to stop lying. I know, lying is fun and easy and sometimes it gives you a shiver of delight to let untruths fall from your cherry lips and watch those simpletons fall in line but no. On the second, max third date, casually say, “I’m dating more than one girl right now, but I think you’re amazing and really special.” Or some shit like that.

She should feel like the only girl in your life, even while she knows she’s not. Make eye contact. Ask follow up questions. Learn what movies she likes, what books she reads, who her friends are, how her family is doing. Human connection type stuff. Stay focused on the positive. Neither of you should take on each other’s baggage.

Or call, email, tinder, dm, or telegram. Nothing. This is your time together. Better yet, put your phone on silent while you two are together. Get your eyes off that little screen and onto the gorgeous person who you have tricked into liking you. Living in the moment: not just an inspirational quote posted by assholes to Instagram while they’re not living in the moment.

Knowing you are dating other women in the abstract sense is very different from hearing how bomb Rachel is in bed or where Tyler works. Offhand comments cut deep and can seriously hurt a girl’s feelings. If she asks pointed questions, keep your answers brief and try to change the subject. You don’t want her obsessing.

Try not to double book, aka hang out with more than one girl in a day. If you really want a twofer, make sure you have at least a couple hours in between rendezvous. People have a way of sticking around longer than you think they might or showing up earlier. One time, my roommate had one girl over and another girl on the way. She didn’t want to hurt the first girl’s feelings but needed her out right away. So, she did what any rational person would do: pretending to remember a pressing errand, got in the car, drove around the block a few times, and then came back to greet girl #2. Should you over schedule, this is a cunning solution.

Don’t post pictures of any of the girls you are dating. Don’t tweet about any of the girls you are dating. Don’t write cutesy statuses about the girls you are dating. Cute couple pics are an instrument of terror reserved for actual couples.

The playing field upon your snatch must be even. According to my roommate, “I don’t give gifts because I don’t want to give one girl something that another girl doesn’t get. That’s playing favorites.”

“You can love more than one person,” my roommate states. Very true. Just remember that loving someone is different from being in love with someone. I love my cat, but I’m not in love with my cat. Wait. JK. That’s a bad example. I am deeply in love with my cat. Moving on.

After you’ve established a solid rotation, there may come a time when this sexxxy merry-go-round feels like a broken roller coaster in an abandoned amusement park. This is the time to get off. Throughout each dalliance, regularly ask yourself: “Does this girl make me feel better or worse? Does this relationship bring joy or stress? Do I want to bang her or is it more an obligation thing?” Weigh your feelings. Be mindful of her happiness. Listen to your gut with Bush-era consideration.

Relationships only end in two ways: a breakup or death. Casting aside anyone’s imminent demise (this isn’t television), you should know how to break up with class, consideration, and an extremely firm hand. Take her to lunch and say something like, “I adore you as a friend and feel like our relationship should be platonic. We cool?” If she responds, “Yeah, we cool” then YAY you have a new friend whose boobs you have already seen and enjoyed. If she replies, “No, bitch. We not cool af,” then it’s time to go go go. Chop chop.

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