How Do I Snag A Super-Rich Boyfriend? Ask A Pro

Time for more of your most burning questions. Email me about life, love and rich assholes at Happy 4th of July and more importantly, happy birthday to me!

Hi Head Pro,

So I like come from a well off family. (They pay for tuition, most living expenses, etc.) but I just started talking to a guy that is like Brody Jenner rich and the girls he hangs out with are Paris Hilton rich. Compared to them I might as well be fucking poor. I’ve never felt so lost about a situation. I know he like obvi has to like my personality and stuff if we are to actually date and money doesn’t matter but not being able to keep up money wise really sucks. Obviously I don’t want him to be my sugar daddy (well I do but we’re way too early in for that). Please help!!!

Not rich enough betch

Oh no, anything but Brody Jenner rich. There’s something very off-putting about a person who, despite their family being able to pay for all of their college expenses, can say with a straight face that they “might as well be poor compared to them.” I mean, really. Anyway, how in the world you found yourself at this school for the mega-rich aside, the good thing about those kinds of people is that they HATE discussing money. Like, there is literally nothing more distasteful to them than asking what kind of interest rate they got on their yacht because you’re thinking about picking up a second one yourself.

I don’t see it being an issue, at least not between you and him, unless he’s asking you to go dutch on chartered flights to Fiji. Typically, when guys ask you out on dates, they do so with the expectation of paying. The only problems you may have will be with the other girls in his circle, given that you aren’t able to afford purses made from bottlenose dolphin leather. That will depend on how bitchy they are, which, given my limited experience with people in the upper crust, doesn’t hold a lot of promise. Just don’t make a point of bringing it up. You’re probably more worried about it than they are. Very rich people don’t really worry about anything, you see.

Hi Head Pro,

Your advice is awesome, hope you can help me out. I dated this guy last summer, and I was really into him but he was definitely not as serious about me as I was about him. Maybe it was because he was headed off to college, maybe because our relationship was pretty sex heavy from the start and resembled more of a fwb type of thing…. whatever it may be, I want to know why he never loved me or was serious about me; I think knowing if it was some aspect of my personality or just him being emotionally unavailable would give me peace of mind and help me have more healthy relationships in the future.

That being said, asking him would be tricky as we are still really close friends and fuck buddies. I’m over him, I just kinda want closure on our past relationship. Is it even worth it to ask him, or would I sound insane no matter what I said (kinda hard not to sound crazy when asking a guy why he never loved you).

Can’t come up w a clever nickname for shit

Well, your subject line was “this isn’t a ‘why doesn’t he want to date me’ question,” and yet it kind of still is, only worse. You’re right, there’s no non-crazy way to ask that question. I mean, you can always go the “whatever happened to us, why didn’t we become anything more” route, but you’re not gonna like the answer. Most guys aren’t dumb enough to come out and say something like “honestly, your boobs are just too far apart,” so he’ll give you some vague bullshit. He’ll say something like “Oh, I thought we were both just having fun,” which would make you feel like shit. Or, he’ll say you’re a great girl but he didn’t want to get into anything too serious before college, which is probably more accurate but will also make you feel like shit.

My advice? Forget about it as best you can, because it’s unlikely it was any kind of personality flaw on your part and FFS it was a year ago. When you go off to college yourself, you’ll forget all about him.

Hi Head Pro,

I think you’re smart and probably handsome and wise… will you talk me out of a bad idea?

I have a boyfriend, we’ve been together for two years. He’s great, we have a really good relationship. We get along well and trust each other wholly. I just decided to quit my job to move to be closer to him. Since then, I’ve been having second thoughts. I’ve also been unable to get my cute coworker off my mind. I mean, I gave my notice so I’m out of there in a few weeks, so if I can just keep myself from doing anything until then… But I barely trust myself around him. I want him so bad, I can’t stop thinking about him, and how good I assume he would be in bed. The other day he like stretched in his chair and his shirt rose up over his abs and I basically came. I think – think – that if I wanted it, I could have him. I know I shouldn’t throw away a good relationship like that, but I keep catching myself trying to excuse it. Please tell me I’m an asshole and that even if my boyfriend never knew, it would be a terrible idea. Counting on you.

Send help,
Cubicle concupiscence (thesaurused that, not ashamed)

Thank you, I am in fact all of those things. As for your coworker situation, you should probably get a grip if your relationship really ammters that much. Nevermind the fact that you have no idea whether the feeling is mutual, oh no, you can’t “trust” yourself around him, Rapey McRaperson. Like, look: Plenty of people in relationships spend time interacting with people whom, in a vacuum, they’d very much like fuck. And yet, most relationships remain intact, because they have the presence of mind and cognitive abilities to do what’s right. It’s not a novel concept. I don’t care how hot he is, if you’re really so beside yourself with lust for this guy, the foundation of your relationship probably isn’t as stable as you make it out to be.

You’re an asshole, and even if your boyfriend never knew, it would be a terrible idea. Just go home and masturbate your frustrations away, like normal people do.

Dear Head Pro,

As a former nice girl over the years it has become painfully obvious that nice girls finish last….or not at all. So thank you for your hilarious site and giving the best advice on how not to be Anne Hathaway. While I deff prefer to complain to my therapist about my problems, I think it’s time I get some real advice from the best of the betchiest. To keep it short I basically walked in on one of my besties fucking the SAB I used to hook up with. This SAB happens to be in our friend group so I see him all the time. I don’t know how to go about this, who, when, and where do I confront what I witnessed? And how do I come out on top (not they way she was on top) of this situation.

Rules of feminism advocate

Yeah, I would recommend not taking this kind of problem to a very expensive therapist. It’s not like he was your actual boyfriend, so you don’t exactly have any standing here, or a justification for wanting to “confront” someone. He’s just a shady bro who’s dumb enough to fuck his way around a friend group (same, guilty), so it’s not like some major transgression took place. If anything, you may want to fake-apologize to your friend for walking in on her and Kale or whatever the fuck, since she’s probably the really embarrassed one. Do that, and then maybe, MAYBE she’ll be forthcoming with something like “yeah, I know you guys used to hook up, I hope it’s not awkward.”

That’s about the best you’ll get. Since he wasn’t your boyfriend, you don’t get to piss on him and claim him. Even if your rendezvous involved you pissing on him (no judgement), that’s not how human pee works.


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