Mailbag: Dating An Ugly Person, Bachelorette Party Planning, And “Is It Cheating If…?”


Welcome to the PGP Mailbag, wherein I will answer questions from you, our readers. Send your questions to All topics welcome.

Hey Dill big fan.

So here’s my problem. Like seven months ago I met this girl at school and we started of as friends while flirting a little bit. Lately things have been picking up and we have pretty serious feelings for each other. She could be a long term girlfriend in my mind, but there’s a problem. We both agree that the timing is wrong and we’re both willing to wait, but she could be better looking and that’s kinda holding me back. Personality is a 10 and she’s a lot of fun, but she’s a soft 6 at best.

I also met this girl at a party a few weeks ago, and she’s great. I strictly see her as a friend but we’ve been hooking up a lot and it’s the best sex of my life. She’s fun too, and she’s hot and my friends love her and her friends. I just feel guilty and even though I’m not official with the 6, it sometimes feels like cheating.

So my question is, what do I do? Can I continue hooking up with the girl without feeling guilty? Or do I need to pick one? In that case, who? And is it worth it to date a girl that doesn’t really have the looks if I like her despite the continuous harassment I’d get from the boys?

Thanks buddy hope you can help.

Ugly, or in this case, average looking, people need loving, too. If you have intense feelings for this girl despite not being overly physically attracted to her, then so be it. Go with it.

Howeverrrrrrr, I don’t see you sticking it out with the 6, player. “She could be better looking and that’s kinda holding me back” is a very concerning statement to make before the relationship even gets off the ground. Don’t underestimate the importance of physical attraction, and passion, and sexual chemistry, you know like what you have with the much hotter girl with whom you’re having the “best sex of [your] life.”

I don’t see you dropping down a level in physical attraction and chemistry for the 6 after experiencing the best sex chick. I don’t care how great her personality is. I’d reconsider waiting around for the 6 if I were you. You could miss out on something much better.

And no, I don’t think you should feel guilty for hooking up with other people. Isn’t that kind of the reason you’re not diving into a relationship with the 6? If not, you’re exclusive with someone you’re not even dating, and that’s weird. And a waste.

What defines cheating these days?

Up until last week I had been seeing a guy for about six months. Early on I found some pretty shady shit on his iPad. Let me preface this by saying, I didn’t randomly conduct a search and seizure of his devices. In hindsight, I must have been so smitten with the guy that I hadn’t a suspicion in the world. We were having too much fun together and he seemed totally into me. We weren’t playing games and there was no text or hangout too frequent. We’d send double, triple, quadruple texts, and I don’t ever remember him being weird about his phone. There was never a questionable amount of time that went by that I didn’t hear from him so it didn’t occur to me.

This lasted about two months. I had stayed the night and he left for work early. He’d even given me a set of keys that day. I grabbed his iPad – as he did every morning – to listen to Spotify while in the shower. I sat down on the edge of the bed and swiped to open. My first thought was, “Eugh, porn.” Can’t fault him for that, I guess. But it wasn’t – upon further inspection, what he had left open, was a Snapchat video. No, it was a recording of a Snapchat video. From a girl. From the day before. And it was porn all right. My mind was blown. He had held his iPad over his phone then tapped to open the Snap in order to keep the video.

I won’t bore you with the details of my initial reaction but you can imagine. This was fuuucked up. When I regained consciousness, I opened up his video and picture files and it was more of the same x1000.

It’s obvious he’d had his iPad at the ready because he was expecting a video of that nature. It was solicited. It was very clear what kind of “conversation” they had been engaging in.

I told a girlfriend about it and she said that she has a couple of guys she “talks to” that way (via Snapchat) but would never do so if she was in an exclusive relationship (which I was).

This was cheating right? And this is totally not normal behaviour? Like this isn’t common is it? Do guys do this?

I think the physical act of cheating probably starts with kissing. Emotional cheating is a thing, too. What your guy was doing would fall under this category.

I think the general litmus test when determining whether something is acceptable or not is if you’d be able to tell your significant other about it. Could you tell your SO that you record nudie vids of other people on your iPad and store them for later viewing? Certainly not.

I don’t think I’ll determine whether this qualifies as cheating because that’s for you to decide. But I can absolutely say that this is not okay. People are overall pretty shitty and do shitty things. I don’t think this is “normal behavior” but it’s not surprising, either.

Hey Dillon,

Love the column, and I need your advice.

So this girl and I have been friends since high school (currently a senior in college) and we’ve always been really close. We met because she was dating one of my best friends at the time. They broke up a while ago, but she and I always stayed pretty close. She goes to a different school than me so we don’t see each other very often, but we talk all the time and have recently started talking about a relationship…. I’m not friends with the guy at all anymore and so I’m not sure if it’s okay to go forward with it, along with the fact that we’d be starting our relationship long distance. What do you think?

The long distance thing sucks, but if you’re both in your final year of college and thus graduating in a few months, that would give you the opportunity to move to the same city pretty soon. Not that bad. Not ideal, but not that bad.

Dude, OF COURSE you should go for it. They broke up “a while ago” plus you’re not even boys anymore? You are so far in the clear. If it will make you feel better about things, send the guy a courtesy text, not to ask his permission to pursue his ex, but to inform him that you’re going to. But that’s just a courtesy. She’s expecting you to go for it, too. You better go for it or I will personally drive to wherever you live to fight you.

Hey Dillon,

So one of my sorority sisters is getting married and she’s having a big bachelorette party: 14 girls plus the bride. All of the girls invited know each other because we were all in the same sorority EXCEPT the bride’s sister, the MOH. While the rest of us are in our late 20s and are financially stable, the MOH just graduated from college and is currently unemployed.

The bride announced she wants to do Cancun. In previous bachelorette parties with these girls, we’ve done Napa, Vegas, and Denver so we were all excited about the idea of Cancun (#ThingsGirlsDoAfterGraduation). Then the MOH announced we can’t do Cancun because she cannot afford it. When we pressed her about it she said the only way she will agree to it is if we pay her way. Otherwise, she says she’ll plan a night out in our home town for the party and that’s it.

We’re sympathetic to her situation, but we’re already paying for the bride; we don’t wanna pay the full expenses for another person. So what do you do when the MOH (due to finances) wants one thing and 13 girls (who can afford it) plus the bride want something else? Whose wishes win out?

What a selfish little hoe. Any level-headed person in her position will gracefully bow out of the equation. I understand she’s the maid of honor and a pretty important piece in all this, but when you’re outnumbered 13 to 1 and the decision in the balance is a trip to Cancun versus staying home for a once-in-a-lifetime bachelorette party, you have to do what’s necessary not to spoil the fun for everyone. Plus the bride made it known she wants Cancun.

To have the audacity to suggest everyone else pay her way on top of it? Oh hell no. This chick sucks.

If I were you, I’d let this person know we are going to Cancun and it’s up to her to figure out a way to make it work financially. In a nice way, of course. When you accept the position of maid of honor or best man, you accept all that comes with it, and that includes being a team player when necessary.

Hey Dillon,

Big fan of the page!

So I started dating this girl about two months ago and I really like her! Then I found out through a mutual friend that her best friend’s boyfriend cheated on her best friend with her a few months before we started talking. Now I really like this girl but I am conflicted because if she’s willing to do something that screwed up to her best friend then what are the chances of her doing something like that to me?

Cheating is bad enough, but to be the one your best friend’s boyfriend cheats on her with is next level fucked up and unforgivable. Is there a chance she’s a changed person and would never cheat on you? Probably not.


The more questions I receive, the better this series is going to be, so send me your Mailbag questions to 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. Email:

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