Help, My Boyfriend Insists Upon Using Condoms! – Ask A Pro

Send Head Pro your questions about life, love and condoms to [email protected], and follow him on Instagram at @betchesheadpro.

Dear Head Pro,

I have been dating my boyfriend for four months and we’ve known each other since we started business school a year ago. Things are great, but he always wears a condom when we have sex. I think he is super afraid of getting me pregnant, since we’re both very focused on our futures right now and he’s religious so he would not be thrilled with an abortion (not like it would be his choice anyway).

But I think his fear is pretty unfounded. He knows I am on the pill and that I have made it through life without any “accidents”, so clearly I know what I’m doing. Further, I am in business school too so I am highly motivated not to fuck up my birth control. We have had a talk about it, which included me saying that if we did want to have sex without condoms that I am open to it, but of course we would need to be tested and such first. He responded by reiterating the pregnancy thing.

This strikes me as really odd considering my experiences with ex-boyfriends, who use condoms at first but then want to go without about a month or so in. My boyfriend told me he’s clean and I believe him, so I don’t think he’s lying about that, but I do feel like he is being evasive and the pregnancy thing is pretextual. Do you think his fear of pregnancy is well-founded? Or, do you think he is waiting a bit longer into our relationship to take that step? Or, do you think there is another reason? I am mostly okay with the condom thing due to easier clean-up and most of the time I don’t notice it in the act. But using a condom every time for so long made me realize how much less intimate sex is with a condom. I love him so much and a part of me is sad that he won’t have unprotected sex with me, even though ultimately I know that it is the act and not that specifically which matters. But also, sometimes the friction is uncomfortable.



Dead Con-fused (not bad!),

Jesus, people are fucking weird. Most guys will offer to castrate themselves in front of you if it means not having to use a condom, and the fact that the pill exists means that the whole of humanity has spent centuries developing safe ways to bone raw-dog. To be honest your boyfriend sounds like kind of a square. I mean, it’s great to have priorities and all, but if “he’s really focused on his future” is how you’d describe someone, they’re probably not going to be the life of the party.

I think there are a few possibilities as to why your boyfriend won’t go without a raincoat. One is that he’s a moron who doesn’t understand contraceptives (the business school part makes this plausible!). The pill and other hormone-based contraceptives are far and away the most effective forms of birth control we have, with the exception of the IUD (some of which also have hormones). Condoms are great protection for a lot of reasons, but they’re not the best when it comes to preventing pregnancy. The second possibility is that he has a dirty dick, and he’s not telling you about it. Even if he’s clean, he may just not want to get tested. I cover this a bit more in our upcoming book (shameless plug), but guys are TERRIFIED of STD testing because we don’t have our junk examined regularly like women do.

The third possibility is that he views unprotected sex as a “step” in the relationship he’s not yet ready to take (which is stupid). Finally, it could be that he has a hair trigger and can’t last very long without a condom (legitimate!). Also, while unlikely, if he’s like SUPER religious he may see unprotected sex as something to be “saved” for marriage. You never know.

I think the most likely answer is some combination of options 1 and 2, misinformation combined with a vague sense of uneasiness. The first thing I would do is make sure he understands how contraceptives work, and why taking the pill regularly makes you as safe as you’re ever going to be. Then, work the discomfort angle — tell him that sex with a condom can sometimes be painful, and that his options are to either go without or have sex less often. I have a feeling you can guess which one he’ll pick. At the very least, you’ll get down to the bottom of why he really likes condoms so much.

Kisses (through a dental dam),

Head Pro

Dear Head Pro,

So I recently started hooking up with this guy who is basically an asshole who gets with an insane amount of girls. The only reason I can give you for starting this is that he’s really hot and the sex is really good.  He’s been getting with other people as our thing has been going on, and I have too, so I’d definitely call us fuck buddies.  I keep saying that I’m never gonna get with him again, but I always end up not being able to resist.  We always get in fights and then don’t hook up for a while, but before I know it I’m in bed with him again.  A couple weeks ago he asked me to be his girlfriend, and kept telling me he loved me. 

I obviously said no, because he’s a douche who would cheat on me in a split second. I have to admit I kinda like that he says he has feelings for me, because it makes me feel like less of a slut when we hook up.  And I really have no idea if he’s telling the truth about how he feels about me.  If he is…I could see myself having feelings for him to.  But last night it was completely different.  As soon as I got to the party he pulled me into a room and we barely kissed before doing everything else… And afterwards he was totally an asshole bragging to all our friends about what had happened and giving them details.  I kept telling him to stop, but he wouldn’t shut up.  I told him I wasn’t gonna hook up with him again, but he doesn’t even believe me anymore when I say that.

Is he being real with me when he says he loves me or is he just saying it so I’ll get with him?  Should I continue to get with him despite all of this or do I end it?


Slutty and Confused

Dear Stupid,

I love when girls tout a guy’s promiscuity, as though fucking a guy who will fuck literally anyone is some kind of achievement. It’s like saying “I had lunch at McDonald’s today. BILLIONS AND BILLIONS SERVED.” Anyway, where to start? First, hooking up with a douche you aren’t dating doesn’t make you a slut, it just makes you a moron. Second, the fact that you were getting in fights with this guy should have been all the indication you needed to leave him the hell alone. You shouldn’t fight with your fuck buddy, or at least shouldn’t be fuck buddies with someone you fight with. All the drama of a relationship with none of the security!

I don’t know why his singular, desperate declaration of love (which he immediately proved to be disingenuous) made you think he was turning over a new leaf, but that last act of dickery should be enough to tell you that he doesn’t actually give a fuck about you and never has. Guys don’t embarrass girls they actually care about. Unless you’re able to COMPLETELY distance yourself from him emotionally (“I could see myself having feelings for him” is a nonsense statement, by the way), you’re never going to be able to hook up with him without wanting… whatever it is you want from him (which isn’t actually clear).

I think you need to cut it out for good, through whatever means necessary. I get that he’s hot and fucks real good, but how many times do you need to hear a song before you know on the words, you know?

Douchey Kisses,

Head Pro 


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