This story appears in the September/October 2017 issue of Playboy. Subscribe

Q:How soon is too soon to start dating a friend’s ex? Here’s the story: A year ago, my buddy was sleeping with a girl he really liked. They never made it official, though, because she didn’t like him in that way. (She pretty much broke his heart.) Now, a year later, the woman is sliding into my DMs on Instagram, and she lives only two blocks away. I liked her then and I like her now, so I want to pursue something. By the way, my buddy goes on a new Tinder date every other week, so I think he’s over her.—J.G., Phoenix, Arizona

A:Here’s what I know about men: It’s never too soon and it’s never too late to date your buddy’s ex, because either way he’s going to be ticked off. Blame evolution and men’s deeply ingrained biological drive to dominate when competing for a mate. It boils down to “You’re not going to piss on my tree.”

That’s the bad news. The good news is that culturally, men are indoctrinated with the “bro code” from the time they’re children. Growing up, they’re taught “bros before hos” every step of the way. So men are much better than women at duking it out, licking their wounds and moving on. But your buddy’s frequent Tinder dating is no guarantee he’s over her. My guess is he’s still trying to fill the hole she left when she crushed his heart. So ask yourself how good a buddy he is. If you do pursue her, be prepared for a backlash, and recognize that you might be sacrificing a friendship for an Instagram crush. Is she worth it?

How tacky are bite marks? I’m currently sporting a few that felt hot at the time, but now I’m a little embarrassed about them. Asking for a friend who won’t ask for me.—L.W., New York, New York
Getting bite marks and hickeys is like entering a hot-pepper-eating contest: It’s thrilling in the moment, but you’ll regret it later. They’re tacky as fuck and scream “I’m a teenager discovering my sexuality!” or “I’m desperately trying to prove how much sex I’m having!” or “I wear Ed Hardy T-shirts!” (And I say this with all due respect to anyone who identifies with those sentiments.) Even so, it happens. Fingerprint bruises on the ass, claw marks down the back, rug burn—all this evidence that you just had kinky sex isn’t a great look at your family’s Labor Day barbecue. If you’re into being branded, keep it in places you can hide. Also, if you’re not in an exclusive relationship, potential partners probably won’t be stoked to see remnants of your other, crazier sexual escapades on your body.

I’ve gone on several dates with someone and want to ask her to be exclusive, but I worry I’m not in the right financial position to take the relationship to that level. To start, I have a roommate. I know some women look down on that, so I haven’t even brought her home. Am I being overly sensitive about my circumstances?—D.B., Topeka, Kansas
Yes and no. I have a lot of compassion for men, because despite third and fourth-wave feminism, you’re still expected to be big-shot providers. Women still want a guy—a baller—who can pay the bill even if they want to be able to pay it themselves too. So I understand why your financial circumstances might make you feel insecure, especially given our capitalist society’s tendency to equate one’s value with one’s bank account.

You have to ask yourself what kind of woman you want. For women who require a certain kind of lifestyle, the fact that you don’t own a home would be a deal breaker. That’s fine. Other women value substance over materialism. If the person you’re dating judges you for having a roommate (assuming this roommate isn’t your mom and you’re living in her basement), she might not be the right one for you. Figure that out before you even contemplate something as serious as an exclusive relationship.

Is it possible to be in love with two people at the same time? I’ve been casually dating someone for three months now, and on a few occasions “I love you” almost slipped out of my mouth when we were saying good-bye. So I know I love her. But I’ve also realized that I’m in love with a friend of about a year. I can’t stop thinking about either of them. What’s the difference between love and infatuation? I’ve never felt so conflicted.—K.H., Dallas, Texas
These are two separate questions, so let’s start with the first. Yes, it is absolutely possible to be in love with two people at the same time; the practice of polyamory is based on this idea. I suggest you look into poly. It will turn you on to alternatives to monogamy and you’ll also learn about a radical approach to communication, honesty and transparency that can be applied to any relationship.

And of course you feel conflicted. You’re trying to pin down a feeling—love—that’s as deep, vast and changing as the ocean. Love is a shape-shifter: It can be the warmth you feel for a child or the familial devotion you have for a sibling. It can be delirious and messy, like infatuation, or hot, passionate and short-term. That same infatuation may then turn into friendship, which then evolves into deeper affection. Try to pin down love and you lose. Let it be.

Your challenge is to remain honest with both women and, more important, yourself while love does its thing. You have a lot of questions to answer, but first is whether either woman feels the same way about you. Start there.

I consider myself a romantic guy, but it seems the more romantic the gesture (e.g., randomly sending flowers and “good morning” texts), the more a girl backs off. Is negging the new chivalry?—C.O., Chicago, Illinois
No. Chivalry is the new chivalry because it died sometime around 2005 when Neil Strauss published The Game: Penetrating the Secret Society of Pickup Artists and courting a woman morphed into just picking her up. Negging is lame. Most smart, modern women are savvy enough to see through that shit. Over the years, we’ve developed strong immunities to stupid tricks. Don’t resort to playground tactics. We’re adults here.

Unfortunately, many women I know have become so distrustful of male advances that they sometimes view even straightforward romance with skepticism. You have to be willing to put in the time it takes to earn a girl’s trust. There’s also such a thing as doing too much, too soon, which signals that you may be co-dependent, controlling or needy. She might also just be one of those women who are into assholes, which is her problem, not yours. Consider some rejections a blessing. Go easy. Unless you’re bombarding her with flowers and texts like a psycho, keep being your charming self. Eventually you’ll attract a woman who appreciates your old-school values. It might even be me.

Woman to woman, what’s the best way to tell a boyfriend he’s not a great lover? We have sex, and I’m attracted to him, but I feel my body is simply a vehicle for his orgasms. The way he positions my legs, the focus he gives me during sex and his interest in helping me come after he comes all need improvement. I love him, but his lackluster sex skills are his worst quality.—K.A., Bangor, Maine
Telling a man he sucks in the sack requires the finesse and skill of a bomb defuser. A man’s identity is intertwined with his sexual prowess, and broaching the subject will expose you to booby traps, remote detonations and ambushes from his ego. Proceed with caution.

Men aren’t taught how to fuck. We have to teach them—gently. Don’t bring up the subject in the heat of the moment (do it over brunch or dinner instead) and don’t say anything that will put him on the defensive. If you make him feel like a failure, you’ll set the stage for all sorts of interpersonal problems, such as performance anxiety. Ask if he’s willing to explore some new techniques in the bedroom with you. Make it about the two of you getting to know each other better. Express that you want to focus more on your orgasm, your pleasure. Most men are responsive to the idea of improving their skills.

Worst-case scenario, you’ve fallen in love with a selfish asshole. You’ll never be satisfied, because you’ll either grow resentful or end up looking outside the relationship to meet your needs. If that’s the truth, fuck him—then get out.

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