Should I Forgive My Guy For Cheating On Me After I Tried To Make Thing Serious? Ask A Pro

By The Head Pro

Dear Head Pro,

I met this pro in the spring and dated him through the summer and into fall. He was pretty successful through a family business and was about a decade older than me. We got along great, I met a bunch of his friends and family, and we had a lot of fun together. He was always a really good guy, never made me pay on dates, was romantic and treated me with respect. We started seeing each other 2-3 times a week, and talked almost every day.

I started getting really freaked out after the months dragged on and there was no title in sight. I tried talking to him one day when we were going on month 5, and he was honest and said that he wasn’t looking for anything serious. He was hesitant to commit to anyone because he had such a bad break up with his ex about a year before, and had thought she was the one. He said he had dated one person after her and before me, and that when he met me he stopped talking to her.

Right after this convo, I went on vaca for two weeks before starting my new job in finance. When I got back, we met up again and talked more. He told me our talk had freaked him out, and while I was away he fucked someone else.

Needless to say, I ended it. He quickly moved on to dating another girl (a bartender in a club), but I want him back. Not only is the jealousy killing me, but I feel like I made a mistake by pressuring him and ultimately pushing him towards someone else. He did all the right things, and I feel like I over-analyzed it because it wasn’t progressing as fast as I wanted… to the point where I ruined everything, and nothing was wrong but I created a non-existent problem.

Is it worth it to try and get him back, and blame it all on my new-job anxiety? Or should I let him go and try to get over my regret/jealous feelings?

Please help.


Summertime Sadness

Dear Lana Del Ray is Terrible,

Jeez, what is it with girls dating way older guys lately? There’s nothing like the old “I got scared so I stuck my dick in the first thing that moved” explanation. This is obviously a real thing that happens all the time, as any woman who’s watched a scary movie or visited a haunted house with several men can attest to being downright BESIEGED by dicks. That ridiculous notion is all you need to realize that this guy is full of shit, and you didn’t really do anything wrong.

If your totally normal conversation “freaked him out,” that’s a sign you’re dating an overgrown man-baby with a wallet, not a sign that you’re coming on too strong. Not after five months, at least. No adult should have that much trouble applying a label at a sensible point in a relationship, as though he’s a high schooler asking his homecoming date if she wants to “go steady.” Trying to somehow conflate the notion of applying a label with the failure of his last relationship is deeply, offensively stupid. It’s like saying you got a bad grade on a paper because you gave it a shitty title.

So, no, he’s not worth “fighting” for. I mean, look at who you’re considering pursuing - a supposed grown man who immediately fucked another girl after you expressed genuine interest in him, who then moved on to dating yet another girl (I assume exclusively, since you’re so jealous) after explicitly stating he didn’t want anything resembling a commitment. Do a bunch of free dinners (50% of what you say qualifies him as a “really good guy”) really justify putting up with these bullshit juvenile antics? No. Generally speaking, it’s never worth it to try to win your ex back. Things always end for a reason, even if the real reason is buried beneath a false one.

Nice name-drop on your career field,

Head Pro

Dear Pro,

I am madly in love with my neighbor and brother's best friend. He's known me since i was 2, and he's 4 years older than me. We now live in the city close to each other, and hang out all the time, and I totally consider him one of my best friends. I always get flirty vibes from him and my friends/his friends always ask me if we're hooking up, but we never have.

Recently I had sex with his old college roommate and his really good friend, and he doesn't seem to mind at all, he actually encourages it by telling me he's a great guy and he's going to be super rich someday. Does this mean he's totally not into me?

I've always thought he's just seen me as his best friends little sister and the girl who lives next door, but I'm not so sure anymore. Part of me thinks he feels the same way as I do, but he doesn't want to ruin what we have either. Every time we're together I want to tell him what I'm thinking, but I'm terrified of losing one of my best friends. I'm not sure if it's worth the risk of telling him how I feel.


Getting Mixed Signals

Dear No You’re Not,

You know, I’ve always said that if you want to show someone that you’re madly in love with them, you should fuck as many of their friends as possible. It’s like sexual bingo - the freespace only counts if you can fill in the whole row. In a situation like the one you’ve described, I think you’re reading too much into normal, familiar male-female interactions and calling them “flirty.”

As I think I’ve mentioned before, I have a sister who’s several years younger than me, so I’ve been in a similar situation. Random chance dictates that some of her friends are bound to grow up to be hot babes, and the whole “I have the hots for my friend’s older brother” thing is a cliche at this point. Once everyone reaches adulthood you at least become aware of the fact that it would be ok to touch each others’ parts from a legal standpoint, and yet I don’t know anyone (myself included) who’s actually bagged one of his sister’s hot friends.

It’s not just the “I’ve known her since she was in diapers” thing, though that plays a part. It’s more that there’s too much familiarity. It would be weird to date/hook up with someone that (in this guy’s case) your friend knows better than you do, because they’re related. It’s mixing friends, family and significant others in the strangest, least-comfortable way. Interacting with your girlfriend’s male relatives is weird enough on its own, to say nothing of everyone knowing each other since early childhood. That’s why, at best, you’d fall into a very brief (perhaps even one time) fling, because all the lust in the world can’t overcome the inherent weirdness.

I doubt he’s so much flirting as he is acknowledging that he finds you attractive and that perhaps in another universe, things could have been different. He’s encouraging you to continue seeing these people because if nothing else, it solves the problem for him. The good news is that if you really think you’d feel better expressing your feelings, go ahead - he probably already suspects as much. Maybe don’t lead with “I am desperately in love with you,” but it would be cool to discreetly let slip one night over drinks that you always had a crush on him growing up. You never know what might happen. There are exceptions to every rule.

Brotherly Kisses,

Head Pro




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