A Gentleman's Guide to Dating Multiple Women

Dating one woman can be challenging, so it goes without saying that dating several women at a time can pose many potential obstacles—the biggest being not making yourself look like a complete asshole.

Here's how to maintain your integrity, even if monogamy isn't in the cards, with our Gentleman's Guide to Dating Multiple Women.

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This is essentially the difference between being a gentleman and being “that asshole.” Womanizing assumes some sort of deception. In contrast, dating multiple women is about being indecisive and actively avoiding monogamy. It has zero to do with duplicity or running game.

She doesn’t need to know about how your still-beating heart was torn from your chest, or that you prefer to sow your wild oats with a minimum of five women simultaneously. What she does need to know is that she’s not the only one. While difficult to say, telling her you’re seeing other people conveys you’re not looking for a commitment, and leaves the decision to get involved (despite the fact that it’s unlikely to lead to a relationship) up to her.

While it doesn't rid you of guilt if you hurt her, it does give her the option to opt out if the terms are not agreeable to her. Present her with the facts, and let her make the decision herself.

Remember how in Pretty Woman Julia Roberts' one rule was, "No kissing customers"? She was a smart woman. She knew that setting something off limits was a way to maintain boundaries, and remind Richard Gere of the limits of their relationship.

Take notes on Julia's technique. You should maintain some level of detachment from the woman in question and draw some lines. For example, if you don't want a relationship, you should probably not spend several days a week together, have sleepovers every night, or make her dinner. Think about which actions might ultimately make your intentions unclear, and eliminate them.

Regardless of what her inquiring mind asks you to reveal, you should keep the details of your activity with other women to yourself—even if she claims she's just curious and insists she won't be upset. Her masochistic inclinations aside, it's your job to not purposely inflict pain on her.

The where, when, and why are between you and the other girl. Sharing the particulars of what you do, even casually ("I just had Mexican with Michelle last night") is tactless, and will leave a bad taste in her mouth. Keep the details under wraps. Nobody cares about Michelle and her gluten-allergy.

Again, there's a difference between being emotionally nonchalant and being a total d-bag. Treat her with respect and kindness, but never woo her with insincere emotions.

Strike "I miss you" from your vernacular if you don't really miss her, and you only miss having sex with her. Clearly, there's a big difference. Don't tell her she "means so much" during pillow talk because it feels good to say and you want to see her smile. Honesty will make her happy. You can keep your half-ass compliments and sweet nothings to yourself.

You may be out there playing the field like Derek Jeter, but your social media feed can communicate another story entirely when your flavor-of-the-night checks into the bar you just walked into, and tags you. Remember what we said earlier about keeping the details under wraps? Thanks to Mrs. Social Media Happy, you've just violated that rule and essentially rubbed her nose deep into your business. It's rude to her, and it makes you look gross. Really.

You're not big brother, so you can't exactly order her to stop using social media. What you can do is make your Twitter, Facebook, FourSquare, and Instagram private, and opt not to accept her friend/follower requests.

Yes, you'll miss out on tweeting her, but you'll gain peace of mind knowing that you're not unwittingly broadcasting the details of your personal life.

Having sex with several women is one thing, recklessly spreading STDs is another. If she knows you're hooking up with other women, we hope she'd insist you wear a condom. But even if she doesn't, you should.

Wear a condom every...single...time. Get tested regularly. You don't owe her a commitment, but you do owe it to her to be clean and safe.

Regardless if you explicitly tell her you're not looking for a commitment, and openly acknowledge you're dating other people, she may still get attached. Emotions don't follow the rules.

If she has feelings you can't return, boss up and end things. Sure, it feels good to be loved. It's nice to have someone who will spend time with you, have sex with you, and not require anything of you. But if you sense she's only begrudgingly playing the part in return for something you'll never give her, let her go. If not for common decency, then for the fact that the aftermath will be ugly.

Maybe it's human nature or because karma revels in irony, but sometimes, despite your best intention to remain stoic and emotionally unavailable, you will feel feelings. Some semblance of concern will creep in. She'll admit she's seeing someone else, and your face with flush with anger.

What, you thought you were the only one who enjoyed the freedom? False. Independent, free-spirited women have been around well before Beyoncé was singing about them. Still, they may surprise you. You might be tempted to tell her she's not allowed to see other people, despite the fact that you also are. Try again, buddy.

She's free to let her freak flag fly, just as you are. If you'd like her to stop seeing other people, you might want to call it quits with your trio of lovers, and tell her your feelings have changed.