Does Sleeping with an Older Man Because He Pays for All My Shit Make Me a Prostitute? Ask a Pro

Most emails I get don’t warrant a response, because they’re stupid or have been answered before. Some are thoughtful but too long to publish, because apparently you think that 1,000 goddamn words worth of backstory is somehow relevant to the question you’re asking (it isn’t). Other times, the emails are dumb but mercifully short, so I answer them mailbag-style, which you all apparently don’t like.

Then there are these emails. The emails too awful for a regular response, but too special to be totally ignored. These are the emails I’ve kept tucked away all year, just waiting for the right time to share them. That time is upon us. Behold, yet another in a series of contenders for the best email of 2013.

Dear Head Pro,

So this internal dilemma I'm having all started a couple of months ago when I met an older gentleman (50-years-old to my 22) at work and he asked me to go see Book of Mormon with him. He was very forward, which I liked, plus funny and handsome in a blue-eyed silver fox sort of way.

We've been on dates almost every week since then (he takes me to charity events and the opera and broadway shows and out to really nice restaurants). He started taking me shopping, and then things spiraled and all of the sudden he was paying for all my spa treatments and my gym membership and a personal trainer. As much as I enjoy spending time with him I know wouldn't be doing it if it weren't for his money.

On our most recent date the fact that I hate my job and I've been looking for a way to quit so I can pursue my dreams or some shit like that came up. He offered me “an allowance” to make that possible. If I sleep with him now does that make me a hooker?


Potential Prostitute

Dear Potential Prostitute,

Yes, it does! Not, as you might imagine, simply because he’s older (way, way, grossly older) and giving you money. It makes you a prostitute because you said yourself “I know I wouldn’t be doing it if it weren’t for the money.” So, all of that time you wasted talking about how funny and handsome he is was bullshit. If he were all of those things, but poor, you wouldn’t be with him. Money being the key driver of your relationship makes it transactional, and when sex becomes part of that transaction, you by definition become a prostitute, at least in one sense of the word. If sleeping with him leads to greater financial gain, then you become a prostitute in every sense of the word.

There will be people in the comments saying shit like “whatever, a girl’s gotta eat!” or “who cares, just do whatever you want if it makes you happy.” Fuck those people. Continuing a relationship because of money makes you a shitty human being, period. Now, I understand that as a white male, I’m afforded opportunities for advancement in life that might not be as available to women, but we’re not talking about any kind of meaningful success here. It’s extra spending money in exchange for fucking an old man who knows he has no business being with you if not for his money. In many ways you’d be worse than an actual prostitute, because at least with hookers there’s no pretense. Everyone is openly aware of what’s going on.

The fact that you accepted the advances of someone his age is revolting, yes, but alone isn’t the problem. I mean, I guess relationships like this can exist, however rare they might be. I understand being 22 when life is one big #yolo tweet and boys your age are dumb and you’re likely kind of broke. I get the “hey, why the fuck not?” thing, I do. Still, you know this is going to lead down a path which you’d rather not travel. If you want to date an older guy, maybe start with someone who’s like 30. Someone in the comments will spout off about how they were 24 and their husband was 50 when they met. Great. Hey, guess what? Your husband will likely be dead before your kids graduate college.

May-December Kisses,

Head Pro


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