How Do I Deal With a Workaholic Boyfriend? Ask a Pro

Dear Head Pro:

Is this guy I am seeing really a douche?  I am 20 and he is 22 and I have been seeing this guy for a couple months.  On one hand he can be really sweet.  He texts me regularly and we hangout out weekly.  He asked me to be his Valentine and asked my friends what wine I drink, bought me chocolate and even a card with a message about how I was his first Valentine.  He mentions going on double dates with his roommate and his girlfriend, has talked about what we both want to do when we graduate and where we will both be and he has planned really thoughtful dates like teaching me to skate and walks along the waterfront.  We get along really well and there is chemistry.

On the other hand, he can also be a bit shady.  When he texts me sometimes there can be hours between messages.  He doesn't take me on dinner dates or out very often – usually its just a movie at one of our places. I have not met any of his friends except his roommate. We have not slept together as I haven't slept with anyone before.  In the beginning he was really understanding of that and didn't push it, but was sleeping with someone else since I wasn't ready.  After this situation was resolved and we agreed he wouldn't hook up with other people he tried to pressure me into hooking up with him.  When I didn't hook up with him he ended up being really mad about it.  When we resolved both of those situations he only apologized after I pointed out he did something wrong and never stated what he was actually sorry for.

Does he actually care or is he just trying to get it in?

Delusional Dater

Dear Delusional Dater,

Unfortunately I don’t think you’re dating a douche so much as you are a typical 22 year old guy. Well, kind of. The acting like a boyfriend and growing weary of your chastity parts are pretty typical. The whole “I’m going to fuck other people since my girlfriend isn’t putting out” thing is pretty douchey, though. That’s not really how that works. There isn’t a relationship loophole that allows you to obtain sex elsewhere because your girlfriend chooses to abstain. That’s just plain vanilla cheating, and I’m kind of surprised you’re still with him. You probably shouldn’t be.

It’s fine, even understandable, for him to grow dissatisfied with the sex situation. He’s a sexually active 22 year old senior in college, and at that particular stage in life it’s not like he has much else to worry about. However, it’s not ok to take those frustrations out on your alleged girlfriend. You knew the score when you entered the contract, fucko, and it’s shitty to now turn that on your girlfriend as though it’s her problem. It’s not her problem, it’s expressly his – you’re not having sex, which is how you want things to be. He’s also not having sex, but would like to. If he wants to have sex that badly, he’s free to do so – just not while he’s with you.

I don’t entirely blame your boyfriend if he wants to end things in the interest of finding someone to fuck, because it’s a lot easier to say you respect those kind of choices than it is to actually do so, and different people have different priorities. But unless you want an increasingly bitchy boyfriend, I’d take the initiative to someone who’ll actually respect those choices rather than go through the motions hoping you’ll decide to roll back the stone blocking the garden tomb.  As I’ve mentioned elsewhere, those guys are out there, just not quite as many of them.

Chaste Kisses,

Head Pro

Dear Head Pro,

I have trouble giving head to people. Since you're the “head” pro I figured you can give me some tips. Some Quote 'Head TIPs' Unquote 😉


I suck at sucking

[Throws computer into ocean; boards rocket ship bound for Mars]

Just a little intermission to give you a taste of what I deal with. Moving on.

Hey Head Pro,

What's the difference between a pro and workaholic in your opinion? I've been dating a guy on and off for quite some time who works full time, is completing his MBA and is now applying for Ivy League law schools. I'm obviously attracted to his high ambition, but he has literally no time to be in a relationship while he is working this hard. We care about each other but are constantly fighting because I'm so tired of continuously coming in second place. Is it better to be supportive of his career choices and hope we make it long term, or dump him for a guy who will actually give me the time I crave?



Dear Want it All Betch,

Christ, what is he even planning to do with all of those accreditations? Start a fucking full-scale, Wal Mart-sized company? I don’t think I care enough about anything to do that much schooling, especially when you don’t even get a “PhD” or “MD” by the end of it. I guess, though, that he should be lauded for his ambition to accumulate U.S. deficit-levels of debt that no job could ever adequately pay back. I don’t blame him for wanting more assurance in job market, but he does realize that his immediate and near-future earning potential is the same with one of those degrees as it is with both, right? I don’t see the value of going $400k into debt for what he could get for half of that.

Anyway, you have to conduct your own kind of cost-benefit analysis when deciding what to do. You have to decide whether or not it’s worth it to spend much of your 20s essentially alone (but not free, either) in exchange for the somewhat uncertain possibility of a prosperous life later on. If he’s going part-time, it’s going to be even longer than that. When you’re evaluating that, you have to consider how into it you are now and whether or not you could see each other growing together. The fact that you’ve been together “on and off” for “quite some time” isn’t particularly encouraging. If I were considering hitching my wagon to someone while they toiled in academia for the better part of a decade, I’d want at least some gesture of commitment.

If you’re fighting now (and things won’t change anytime soon), I can’t imagine that any future payoff could make the mental stress worth it, but that’s me. But if you’re already asking the question, I have a feeling you probably know what the right answer is, for you.


Busy Kisses,

Head Pro


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