Mailbag: Dating, Austin, And Bachelor Parties


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

Sup Dillon,

You seem to be the pro, so I am going to ask you.

My group of friends is planning a weekend Bachelor party and I can’t seem to agree with how the best man is planning it.

Logic says, everyone chips in for the hotel and the group covers the Bachelor, which I am totally fine with. However, the organizer is insisting all attendees pay for EVERYTHING up front, gas, hotel, restaurants, bottle service, lunch, the whole shot.

I suggested that all the guys chip in on the house we are renting, and each chip in 40 bucks to cover the bachelor (imo, more than enough).Said organizer also called me out for not being a team player for questioning his method. Am I a bad person for not wanting to over pay up front for a club that I will likely be too drunk to get in to, or for a lunch I will probably be passed out for.


Every bachelor party I’ve ever been to, everyone pays for their travel and lodging up front, including the bachelor’s. Just split his part among the 8-12 of you and it doesn’t add a whole lot to your bottom line. He gets a free ride. That’s standard.

Paying for everything else, though, that part can be handled a few different ways. For my friends, there is usually one of us who will put everything on his card for the whole trip — golf, dinners, bars, Ubers, etc. He gets to stack Southwest miles and we get to leave our credit cards in our room for weekend. When we get home, he divides the total up and sends us Venmo requests. It’s just easy and it works for us.

I’m not into the idea of asking for money upfront, though. It seems a little sketchy. There’s no telling how much you’re all going to be spending on this trip. If he’s insistent that he’s not the one covering the cost of everything, then it should be an every man responsible for himself situation. Then take turns picking up the bachelor’s tab or something. Like why you trying to hoard all this cash, dawg?


I think I’m correct in my understanding that you’re a native of Austin. My question is; what does Austin do better than every other city? It’s something I’m curious about with every major city, but Austin in particular. It seems like a pretty unique place being a blue dot in a red state (I think), a college town as well as a capital city. I’ve watched tons of food shows, SXSW recaps, etc about it. But I’d like to hear a regular ass dudes take on it. Keep up the good work.

Austin is the Live Music Capital of the World, so a unique thing about this city is the live music. It’s everywhere, not just at Austin City Limits and South by Southwest. From massive concert venues to hole-in-the-walls with a seven by seven-foot stage, it’s just everywhere. It’s a young professional’s city, too. Lots of tech companies have made Austin home and it has attracted young adults who like to party. It has a pretty amazing bar scene that I’d put up against any city in the country.

And like you said, it’s a pretty liberal city. Tons of hipsters live here and transplants from different cities. Just a wide array of demographics. I’m into it. I tell people I was born here and they give me side eye like I’m making it up or some shit.

Summers here are miserable, though. For real. It’s my worst nightmare.

Hey Dillon,

Big fan of you and the whole Grandex fam. Before I proceed with my issue that led me to reach out to you, I need to know something far more important. What’s your beef with “Closer” by the Chainsmokers? Why do you have no love, man? Who hurt you? Song’s a complete jam, especially at the bar around 12:38am, but I digress.

Anyway, I come to you for advice pertaining to a potential suitor. I’ve been seeing this guy for an exact month and I’m into him. We met at a mountain house through mutual friends and it was an instant connection. Not my usual type, super quirky and a little dorky – but he cracks me up and is pretty nice on the eyes. Only issue, he lives 2 hours away. I’ve hung out with him every weekend thus far, spending ultimately every second of the weekend together. We text throughout the day, but nothing of much substance. Mind you, I recently got out of a 3 year on again-off again relationship, so I’m not looking for 100% commitment. On the other hand, I find myself turning down Bumble dates, behaving myself at Happy Hour, and leaving guys on Read because I’m so hung up on this dude. No clue if he’s just looking for a consistent weekend in fun and strictly that, or if he wants to take it slow and maybe build it towards something stronger. I don’t want to ask in fear of seeming clingy or that I expect more out of this. I just need to know, am I wasting my time with a guy who I only see on the weekends? Should I ask what’s going on between us, or just let it play out? I’m going to trust your advice on this one.

Keep up the good work, love the site. Thanks in advance!

“Closer” is hot garbage and I will think less of you as a person if you enjoy it. It’s that bad. It’s THAT fucking bad. “Paris” is worse, though.

You need to broach the subject. Stop trying to guess what’s going on in his head because it will drive you crazy, and no one wants to catch feelings if the other person isn’t going to get there. Just ask him. Communication is an awesome thing. If he gets weird about it then you’ll have your answer and you can slowly start fading him.

Just ask him in a cool, casual way. Don’t be all serious and sit him down like you’re about to tell him his dog died. Just bring it up during a high point in conversation and be cool about it. You’ll get your answer.


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.

Email this to a friend

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:

15 Comments You must log in to comment, or create an account
Show Comments

For More Photos and Content

Latest podcasts

Download Our App

Take PGP with you. Get

New Stories

Load More