Should I Do Anal With A Guy Who Doesn’t Love Me? Ask A Pro

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Dear Head Pro,

I lost my virginity to this guy that I really liked and I thought he liked me and things were going well for a while… But then he started dating this bitch ass girl and yada yada yada, I still have feelings for him but I know I can't be with him. Anyways, we fuck around and he asked me to do anal and I don't know, just wondering what you think about this situation?? I still love him (obviously) and I just don't know what to do.

Betch who is confused in love

Dear Confused in Love,

What the fuck? This is one of those “spit your coffee out” emails. In short, no, do not have buttsecks with this guy. I understand the being in lurve part (however asinine (haha) it may be in this situation), but I fail to see what’s “confusing” about letting this guy root around in your pooper.

People have varying opinions on anal, ranging from “ew no, never” to “it’s my favorite way to greet new acquaintances.” Regardless, and regardless of how “special” you view sex, there’s something distinctly more intimate about buttfucking for myriad reasons. That makes it all the more dehumanizing, I would think, that this guy who’s dating some other “bitch ass girl” wants to use you and your ass as his literal fuckdoll.

Unfortunately, sometimes there’s no avoiding the whole “I’m in love with the guy who took my virginity” thing, but: Dating him doesn’t make this other girl a “bitch ass” (though it does make her an idiot, in this case), and letting him fuck you in the ass won’t make him like like, love or respect you. If anything, it will lead to the opposite. Stay the fuck away from this guy.

Image search “anal prolapse” if you’re not convinced,

Head Pro

Hello Head Pro!

I met this guy a little while ago, and he gave me his phone number.  We have some mutual friends, so he was not a complete stranger.  We would text back and forth sometimes to talk about hanging out.  He made it clear to me then that he just wanted sex, which was fine because I am in no rush to get into a serious relationship at the moment.

We finally got to hang out one night, and had a long talk and make-out session.  The next day he was texting me and revealed to me that he could see us being together, and that there was “something there” since we talked quite a bit.  When I asked him if he still strictly wanted sex, he said that he could see more in the future and that I was “pretty badass.”

He was texting me everyday since the first time we hung out, and we even hung out again about a week later.  During this meeting, he told me he wanted to try to take me on a real date (since it was much like the first).  He has told me that he likes me several times, but he's not texting so much anymore.

I am trying not to get too involved since I have no idea where this is going.  I have gotten mixed advice from several of my male friends, so I need the help of the Pro!

Thank you!

Dear Thank You!,

God dammit with the double spacing after periods. Anyway, I’m a little confused here. How, exactly did he make it clear he only wanted sex, and then why did you agree to hang out with him anyway, even if you’re “not looking for a relationship?” It’s like those scumbags on campus with the free t-shirts: Even if that’s all I want, I don’t take one because I know all they want is to fuck me in the ass with a high-interest credit card. Also, congrats on being the first person in history to say you don’t want a relationship and then throw that out the window as soon as a guy expresses interest. You had us all fooled!

I don’t see how this is different from any other scenario – he, a guy who barely knew you, was down for sex. I mean, isn’t that what we all do when evaluating strangers? Do you see hot guys and go “man, I’d love to know what he thinks about the situation in the Middle East?” No, you say “yeah, I’d hit that.” Then, lo and behold, he hangs out with you, gets to know you a little better, and now he likes you! This is how all relationships start. Sexual interest is the ignition, personal interest is the spark plug, and then actual sex is what finally turns the engine over.

As far as “not trying to get involved because you have no idea where this is going,” what does that even mean? No one in history, outside of an arranged marriage, has known where a relationship was going from the outset. Furthermore, no relationship has flourished without a willingness to find out where things are going. Like, I don’t know what to tell you. If you like the guy, and he seems to like you, then fuck it – keep feeling things out. You ought to be able to get involved with someone without emotionally committing yourself to them.

I promise you won’t die if it doesn’t work out,

Head Pro

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