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Mailbag: Dating An Ugly Person Who Sucks At Sex, Letting Go Of Your Fraternity, And Meeting People

Mailbag

Welcome to the PGP Mailbag, wherein I will answer questions from you, our readers. Send your questions to dillon@grandex.co.

Hey Dillon,

I’m just going to dive right in because as you can guess by the subject of this email, I have a dating predicament on my hands…or in my bed.

Recently, I started seeing this awesome guy who is in my group of friends (but on the outskirts, not the core group) and his personality rocks. My friends all stand by the fact that he’s “objectively attractive” but personally, I’ve never found him that way until it was just him and I at happy hour one night. We started dating and to my surprise, he checked every box on my pretentious AF and obnoxiously picky checklist.

BUT then we had sex and both times it was just bad. Bad and weird- I’m talking high pitched noises and girlish sounds that weren’t coming from my side of the dirty deed weird. Obviously, I’m going to cut it off with this guy. I’m a big believer that whether its your husband or boyfriend or anything in between, you should want to jump their bones in the laundry room and if that’s not the case then you should move on.

I comment on this site semi-frequently and I often say that I’m honest during breakups. This however, should be the exception to my brutal honesty- but I literally don’t know what to say. I know I can’t ghost or slow-fade because we’re both adults- so my question is what the fuck do I say? And is my mentality wrong- is personality more important?

“Objectively attractive” sounds like something you’d say to a friend who’s dating an ugly motherfucker but you don’t have the heart to tell her. Who even talks like that? You never found him attractive until you got drunk one night, huh? Yeah, dude is ugly. Sorry. You’re sleeping with an ugly dude, which is fine, but don’t lie to yourself.

I agree with you that wanting to jump your partner’s bones all the time is very important. Sexual chemistry is hugely important. There are many people in my life who I don’t want to have sex with. I call them friends.

Just tell him “I’m not really feeling a connection anymore.” That’s the catch-all breakup reason, and it’s technically true. It’s a soft blow, too, so you’ll be letting him down as easy as you can. You don’t want to break up with him and destroy his confidence. That poor, ugly bastard.

Hey Dillon,

So I’m writing in because this is now the third time it has happened to me, and need some perspective. I keep getting involved in situtaionships, as the kids call it, where the guys tell me how great I am, the sex is awesome, we date, and things seem to be progessing towards a relationship. If it gets mentioned they tell me, again how much they like me and how great I am, but that they aren’t ready for a relationship. Okay, that’s fine. Typically that’s where things end. Then a month or two later I find out that they are in a serious relationship with someone else. When I ask about it, I get told that it is nothing personal, and that the timing with me just wasn’t right. Now that this has happened for a third time, I can’t help but take it personally. Looks wise I’m relatively average, not a 10 but also not a wilder beast, am funny, smart, kind, and an all around good person. I frequently get told that I’m the kind of girl you marry and not just hook up with, and yet here I am finding myself being the placeholder before a guy gets in an actual relationship. I feel like that terrible Dane Cook movie, Good Luck Chuck, if you sleep with me you wind up marrying the next person you date. It’s disheartening and makes me question why I’m good enough to sleep with and date, but not be in a relationship with, so I could use a male perspective. Is it really just timing in these situations or should I take it personally?

Thanks!

Yes, you should take it personally. They were ready for a relationship, just not with you.

Guys will look for an easy out as to avoid being hurtful, and to make the conversation easier. Telling you “I want a girlfriend but it’s not going to be you,” while very direct and may be appreciated more by you in the long run, is a lot tougher than taking the route he did. He was trying to let you down easy, which isn’t the worst reasoning, but it’s still wrong.

That doesn’t mean you’re not girlfriend material. It just means you haven’t found the right guy.

What’s up Dorn,

So I just recently turned 21 and my girlfriend is still only 20. I’ve been buying her alcohol but I haven’t been making her pay for it. Should I make her pay for it or at least part of it? Or should I just continue to pay for it with my own money?

Thanks man.

I assume you’re asking this as a poor college student. Are you paying for it because you’re of legal age and she’s not or because you’re the guy and it’s the “proper thing to do”?

Either way, it’s time she starts pitching in some. Alcohol is expensive and I see no reason why she shouldn’t pay for at least part of the alcohol she’s drinking. It’s 2017, after all. Good luck bringing it up, though.

Hey Dillon,

I’ve been a TFM reader from way back in 2011 and moved to PGP since its inception. In undergrad I was heavily involved in greek life. I went to a greek heavy PAC12 school, lived in my fraternity house, went to national conferences, and was on my E-board as a junior and senior. I had the time of my life for 4 years and loved almost every part of it. But as I get farther and farther away from greek life I feel like I’m losing connection to my actual organization. The last class of guys I know from my era walked at commencement today. I feel like I don’t really care much about the history of my nationals, or most of its rituals. The best part about the fraternity was the people I met and the friends I made. I’ll forever be thankful for the times I had and my friends but I really don’t feel a special connection to my letters anymore. I see my letters now and I think of doing dumb shit with my buddies, not of some mysterious ritual or chant from the 1800’s. I know you are a fraternity content creator (#tent) so you’ve had to stay involved but did you ever go through a period where you felt something similar?

All the best

Some disclosure is necessary before I answer this. Yes, I was a member of a fraternity, but I’ve never been all about my fraternity. I joined because doing so meant I’d have a ton of friends and be invited to all the parties. I never cared at all about our rituals or traditions. Not even a little bit. I learned all that shit because I had to. To be honest, I found a lot of it pretty dumb. And corny. And hokey. Even on initiation night, I was not into the ritual aspect of it. I was just ready to drink with my friends.

My chapter recently lost their house, and I simply do not care. Why would I? I don’t live there. The term “brother” even makes me uncomfortable. Like I met you three months ago and the only conversations we’ve had are drunk ones. You’re not my brother, Connor. We just pay dues to the same organization.

I’m probably not the best person to ask this question, as I never actually cared that much. So, it may not surprise you to find out that when I hear of someone being “into” their letters years after they graduated, I think they are total losers. It’s time to grow up and move the fuck on. Miss your friends and the parties and the girls; don’t miss your fraternity rituals and don’t know what’s going on with your chapter. At least not too much. Don’t be a loser.

Dillon,

First off I’m a big fan of Touching Base, you guys keep up the good work.

I have a bachelor party to plan coming up. I have been to/planned a few already but this one is a little more difficult. We are from SC and the groom is currently living in Austin. People would be coming from both locations. I thought about just doing it in Austin but with him living there I feel like we should go somewhere else. I am debating between New Orleans for a blow out weekend or a more relaxed 3 day golf trip and hitting up the Robert Trent Jones trail in Alabama.

Thoughts are appreciated!

Lakehouse_dreaming

If he lives in Austin, you can’t do Austin. The bachelor needs to travel on his bachelor party, even if it’s only one town over. I’m not familiar with the Robert Trent Jones Trail but both those ideas sound great. A golf centric trip and New Orleans are both premiere bachelor party choices. Let the deciding factor be what you think he will enjoy most. Don’t let your golf trip be relaxing, though. Bachelor parties are not for relaxation.


Hey Dillon,

Hope you had a great weekend. I graduate college in a few weeks and it’s crazy to think I’m actually entering the real world. I lucked out and got a job in a new city so I move in about a month or so. I spent most of college enjoying the single life and it just hit me that I have no clue what I’m getting into with post grad dating, but I’m finally in a place where I could actually see myself making time for someone. Any suggestions on where/how I can meet a decent man besides dating apps (because I’ve never used one and am a little bit afraid of them)? Thanks for your time.

Be less afraid of dating apps. They’re harmless and allow you to have control of the conversations without giving your number out. Feel uncomfortable with someone? Un-match and move on.

Aside from dating apps, you have to go out. Get your main bitches together and go to dinner at locations where the clientele is largely young professionals, like you. Unless you’re ugly as sin, like that first girl’s boyfriend, guys will approach. Or you can be the aggressor and make moves yourself. It’ll happen.

___

The more questions I receive, the better this series is going to be, so send me your Mailbag questions to dillon@grandex.co and please put “Mailbag” in the subject line.

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Dillon Cheverere

Dillon Cheverere is the Vice President of Media for Grandex, Inc. Dillon graduated (BBA) with a GPA sitting in the meaty part of the bell curve, not lagging behind, but not trying to show off, either. Golf is his game now. He's long off the tee but can't putt for shit. Email: dillon@grandex.co

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