Should I Take Back My Cheating Boyfriend? Ask A Pro

By The Head Pro

Send me questions about literally anything at [email protected]


Dear Head Pro,

Recently, the unthinkable happened- my boyfriend of two years cheated on me. He was at a party without me, got wasted and hooked up with some rando. He took responsibility and told me right after it happened, and I basically cut off contact after that. However, he just reached out and asked if he could see me to talk, saying he realizes he messed up, he needs me, he'd do anything to get my trust back etc etc. I know it's SO unbetchy for me to still care about this dude after everything, but aside from the shitty ending this was the best relationship I've ever had and I was happiest when I was with him. Anyways I guess my question is am I a complete dumbass if I take him back/is it weak of me to even agree to talk to him? Is once a cheater always a cheater a thing? Let me know cause I'm pretty lost here.

It's a cheetah lol get it? (Pls help me) [Note: She attached a picture of a cheetah. It was a nice cheetah]

Nah, you’re not a complete dumbass. If you’re an adult who’s been dating someone for two years, those feelings weren’t created out of thin air, and won’t magically go away, either. In this case, the decision to end things is as much an intellectual decision as it is an emotional one (as in, you still love him but KNOW that what he did was inexcusable). Personally, I don’t really believe in the “once a cheater, always a cheater thing.” Plenty of people go their whole lives never cheating, until they do. Some people cheat on some SOs, but not others. Some people are absolute fucking dirtbags for a while, and then they never are again. There’s no formula to it, unfortunately.

Does it make you “weak” if you get back together with him? Yeah, kinda, but then again thinking about this from the perspective of a power struggle probably isn’t the healthiest angle. I know that most relationship psychologist types agree that reconciliation and rebuilding is possible, even when infidelity occurs in more serious relationships. Really, I think it boils down to whether you can realistically see yourself trusting him again. If not, don’t bother - in that case, this paradoxically becomes unfair to him. And to you as well, because while this may have been the “best relationship you ever had,” it will be a fundamentally different relationship if you can’t let go and trust him.

I wouldn’t feel pressured to take him back - two years isn’t that long, in the scheme of things (it would take longer than that to give a shit about any of the characters on this season of True Detective). But if you really want to, just know that it can and does work, sometimes. Just don’t hold it over his head, unlike..

Dear Head Pro,

I'm just gonna get straight to the point and admit this upfront: I am a very jealous and insecure person. These qualities aren't very attractive, I know, but shit from my past has led me to be like this and I'm not really sure how to change it, so whatever.

Anyways, my guy and I have been dating for a few months now, and we were friends first and are in the same circle of friends. Way back before we were anything, and made out for the first time, it originally seemed like it was gonna be just a hookup to both of us and nothing more. A week after this, he was out with our friends blackout drunk, and kissed two of my good friends. At the time it didn't bother me because I didn't have any feelings for him yet, but now I cannot seem to let it go.

I mention this to him all the time, and he always just brushes me off saying it was nothing, he doesn't know why he did it, that he loves me and wanted me the whole time not them. But if that were true then why did he do it? I just felt like I meant nothing to him, he just wanted to get with me and move onto better things (they're both prettier than me), but then realized he couldn't (they both had boyfriends at the time) so he came back and settled for having me. I know I probably sound crazy and I've accepted that, but I need an outsider's point of view, is this all in my head and I have nothing to worry about, or do I have something to fret over?


Fuck, I can’t even with this. Have you ever kissed a boy? Would you like it if your now-boyfriend asked you (“all the time”) about boys you kissed before him? ZOMG WHAT IF THEY KNEW EACH OTHER OR HAD A CLASS TOGETHER OR BOTH LIKE THE COLOR BLUE?!?!?!? I’m sorry, but come on. You guys kissed once, then he kissed some other (prettier!) girls, and now you’ve badgered the shit out of him to the point where he says incoherent shit like “when I was making out with those random girls, I really wanted you, the other random girl, the whole time!” Like, stahp.

He’s here, he’s into you and as far as you know he’s not sucking face with your friends behind your back (or is he???). You can’t magically make your dumb feelings go away, but they’re all in your head. Most importantly, leave him the fuck alone about it. He didn’t do anything wrong.

Dear Head Pro,
So my family is well off and I am by no means struggling but there's just something so frustrating in my life that has to do with money. My dad was fairly successful back in the day when people worked on the stock market floor. I know that you think, "oh fairly well, six figures" But no, try seven. About $2 million a year for 7 years and then he made over $1 million overall in the past and preceding years. My problem is that he acts like he makes $50,000/year. He refuses to spend over $30,000 on a car. Call me crazy but I don't think that a jeep is unreasonable when you could easily afford a g wagon. He always claims the government could come take his money any time they want but he's just being unreasonable and cheap asf. I understand trying to raise kids who aren't spoiled brats but he's unreasonable and acts like he is poor when it's the exact opposite. What can I do to get him to cough up more dough that I know he has!? Please help, thanks.


Don't know what to put as my nickname

Look at you, both reasonable and clever! You may be surprised to learn that people still work on the stock market floor (they’re called… wait for it… “floor traders”), and yes, they make a fuckton of money by shuffling even larger fucktons of money from one place to another. Given that your dad is worth somewhere in the neighborhood of $20 million, I’m thinking he didn’t get and stay that way by spending a year’s worth of college tuition on unnecessary vehicles. In 2015, a car is about as trashy as it gets in terms of status symbols - unless you’re being driven by someone else, or have it so well that, like, a fucking Ferrari is something you could literally pay cash for, all a BMW or G Wagon or whatever the fuck does is tell the world that you’re trying too hard.

Kia and Hyundai make pretty nice cars these days; I bet your dad could find a good deal on a nice used one for you. If that sentence made you a little sick to your stomach, then I have done my job.

Send me questions about literally anything at [email protected]




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