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Rules for Dating Multiple Women

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Q: Dear Holly. As a man in my early twenties, I’m nowhere near ready to settle down. I like playing the field, meeting women online, and having lots of sex. I think I treat women well, but my sister recently called me a player… and it wasn’t a compliment. I go in being honest, but some women end up wanting more, so they don’t stick around. Are there rules here cuz I don’t want women to be talking about me, if you know what I mean. – Craig

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A: Hi Craig! Believe me, women do like to talk if they think they’ve been wronged. Let me give you some tips on how to avoid the dreaded bad reputation among the ladies.

A lot of men who consider themselves players pride themselves on their dating prowess. And as a woman, I say more power to them… but only if you go about your business with respect.

We’re living in a hookup culture where casual sex is more acceptable than it has been in a very long time, and women are enjoying their dating freedoms too. I like playing the field just as much as you at times. Here are some guidelines I like to follow.

Tips for Dating Multiple Women

1. Stay organized. Some men can date five women and keep that shit in order, but for others, two is plenty to juggle in their busy lives. Don’t mix up who says what or which date is for what lady. And for god’s sake, never call one woman by another’s name.

2. Date women who also want casual sex. There’s no point being a player who chases women who are looking for something more serious. It’s cruel and just plain bad behaviour. State explicitly what you’e looking for on your dating profile and use sites that are more about sex than romance.

3. Be honest up front. Even if you say you’re only looking for casual relationships on your profile, a girl may get other ideas, especially if you are the gentleman you always should be. Women need reminding of the boundaries at times. If things change and you fall for a hookup partner then another conversation is in order.

4. Be discreet. It’s one thing to let a woman know that your relationship isn’t exclusive; it’s quite another to share intimate details of one hookup to another. Broad details are okay to buddies, but us casual lady players don’t want to hear about what you did last night with your Friday girl… unless it turns us on!

5. Play safe. A player needs to be packing at all times. Don’t expect women to have condoms if you’re looking to get laid. And if you have a brand you prefer—Magnum, ribbed, or non-latex—then provide for thyself.

Hookup Help is a Q&A series. If you want advice or a female’s perspective on hooking up, online dating, relationships, or sex… we want to hear from you. SUBMIT YOUR QUESTION, and who knows, you may appear in the next Hookup Land newsletter. -xo Holly 

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