This story appears in the March/April 2017 issue of Playboy. Subscribe

Q:I was recently dumped by a woman I met at a bar near our campus. We dated for about two months, went out together a lot and had some pretty damn amazing sex, so the dumping came as a surprise. She broke it off via text, saying, “Sorry, but I can’t keep dating a fuckboy.” I’ve heard women use that word in a bunch of different ways. (Even my female friends disagree about what my ex meant by it.) So what the hell is a fuckboy? More important, how do I make sure I’m not one?—A.K., Austin, Texas

A:You’re right to be confused. There seem to be as many definitions of fuckboy as there are English-speaking millennials. Overall, it has become a catchall phrase women use to label single men who exhibit all kinds of failings. Urban Dictionary has more than 600 user-generated definitions that attempt to explain the term. The most popular is “a person who is a weakass pussy that ain’t about shit.” In short, fuckboy is a pejorative, with a definition that changes with every person who uses it.

Originally I thought the term was a synonym for booty call. I used it loosely to refer to whichever man I was using for his dick at the time. But then my last booty call, offended that I’d called him a fuckboy, schooled me: “You ain’t even using it right,” he said. When I asked him to explain, he said he wasn’t a fuckboy because he wasn’t a pushover. Turns out, the idea that a fuckboy isn’t his own man is an important differentiator from a booty call. 

Couple that with the prevailing notion that a fuckboy is exactly that: a boy. My friend Marisa defines one as “a lame-ass dude whose male friends’ misogynistic opinions run his life.” My friend Miranda says, “Any boy who tries to portray himself as a man but has no manly properties is a fuckboy. For instance, someone who lets a woman pay for everything or is not up-front and honest about his intentions.” Amber describes fuckboys as men “who are going to tell you what you want to hear because they just want to get in your pants. He’s not the kind of guy you get serious with because he’s so delusional that you can’t trust him.” 

After diving deeper, then, it seems a fuckboy is part pushover, part womanizing sociopath. Here are some simple guidelines you can follow if you want to avoid being put in that category:
1. Do what you promise you’re going to do and text when you say you’re going to text. Don’t flake and then slide into her DMs later. 
2. Be present. Classic fuckboy behavior is being glued to your phone when you’re on a date but unresponsive to her texts when you’re apart. 
3. Don’t beg for nudes.
4. If you like a woman, take her out in public and introduce her to your friends.
5. Misogynistic and homophobic behavior are red flags. Phrases like bros before hos belong in the 1990s. Leave them there. Evolve your gender. 
6. If you have no intention of being in a relationship, be honest. Find yourself a fuckgirl. (They’re out there.)
7. If you vape, brah, you’re probably a fuckboy.

No matter how many definitions and opinions exist, this much is true: We women know a fuckboy when we see one. If the woman you were dating called you a fuckboy, she probably had a pretty good reason.

I’ve been on three out-of-this-world dates with someone I met at a friend’s party. On our last date, things started getting hot, so I asked if she wanted to go to my bedroom. She declined, saying she’d just started a course of celibacy. For 90 days. I’m not sure I’m ready to commit to someone for three months without sex. Should I stay, or should I go?—R.S., Los Angeles, California
 It depends on what you want out of this. If you’re not looking for a relationship, get out. Why bother waiting to get your rocks off in the age of swiping? But if you want a relationship based on more than just sex (and it sounds like you do), I’d say she’s worth the wait. Remember, you don’t have to be celibate just because she is. It’s all about being open, communicative and honest early on. If you’re up-front with her about the fact that you’re seeing other women, you’re allowed to have sex with them—at least in my eyes. In the meantime, you can still date your abstinent lady friend, get to know her better and let the anticipation build. But don’t give the impression you’re all about her while you’re shagging other honeys. That will just set you up for trouble later on. If she’s cool with it, now is the perfect time to have your cake and eat it too.

I’m dating a hardcore Republican who is annoyingly pro–President Donald Trump, whereas I’m still devastated by the November election. It’s putting a strain on our relationship. Any advice?—C.H., Euclid, Ohio
If you can’t let go of your loss for the sake of love—or discuss politics like mature adults and reach an understanding as to why she voted for Trump—I suggest ending it before she’s the mother of your deplorable kids. 

The woman I’m seeing doesn’t want to go down on me. When I ask why, she simply says she’s never liked it. What should I do? This has become a major hang-up in our sex life.—G.M., Tucson, Arizona
Run. Get out. Abort. Just kidding! (Kind of.) First things first: Do you go down on her? If you don’t, this question doesn’t even deserve a response. I’m going to assume you do go down on her; in that case, it’s time for a cost-benefit analysis of your relationship. How important are blow jobs to you? I know a lot of women who hate giving head. I jokingly tell them, “Men love blow jobs more than they love you.” How important is she to you? Could she be “the one”? Is this the only thing that’s lacking? And if so, are you willing to live without blow jobs for the rest of your monogamous life? It’s time to be brutally honest with yourself. 

If it’s an itch you really need scratched, you’ll eventually get it scratched somewhere else—outside the relationship. When it comes to dating, one of my rules of thumb is this: Do everything in your power now to avoid being a douchebag later. If you’re both at the height of feeling the feels, it’s worth a conversation. But understand, women hate going down on guys for a multitude of reasons, whether it’s because they have a sensitive gag reflex or because it makes them feel degraded. If she’s adamant about not going down, don’t push it. Instead, realize it may be time to move on to someone who shares more of your interests.

After a long winter of being single, I’m eager to meet someone new. But dating apps don’t work for me, and in my experience, it’s hard to approach a woman in a bar when she’s surrounded by friends. Is there such a thing as a good pickup line?—K.W., Duluth, Minnesota
First, you’re doing it backward. In my opinion, you should break up in the spring and shack up in the fall. Enjoy some summer flings and settle down only when winter’s long, cold nights are upon us. But on to your actual question. 

I’m not going to lie: You’re in a tough position. Dating apps have killed the meet-cute and made it increasingly hard to find opportunities to start conversations with women in public. In fact, the pickup line is such a dying art—in person and online (a 2016 Oxford Internet Institute study found that 49 percent of all messages sent on dating apps like Tinder go unanswered)—that leading with a straightforward, friendly introduction may cause you to be mistaken for a creep. 

That said, if you’re determined to go at it the old-fashioned way, know that there’s no surefire pickup line that works every time. Women can smell phoniness and packaged one-liners from a mile away, so evaluate every woman and situation on a case-by-case basis. A man once picked me up in a coffee shop with a brilliant card trick; another time, a man I frequently saw at the dog park said “We have to stop meeting like this” as we cleaned up our dogs’ shit. It was hilarious and endearing. 

The success rate of cold-calling women in person is based 10 percent on what you say and 90 percent on how you say it. Instead of asking “Can I buy you a drink?”—which assumes a lot—a better question may be “What are you drinking?” Timing and confidence are everything. You got this.


Questions? E-mail advisor@playboy.com.