Mailbag: Bachelor Parties, Austin Nightlife, And History With Your Boy’s Girlfriend


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


I need the noted bachelor party expert for this one:
It has come time for the first guy in my high school friend group to tie the knot. None of us in the bachelor party have ever thrown one before or been to one (fresh grads) and we’re all new to the logistics of a successful bachelor party. We know it will take place at his lake house (dope) however it does pose a few problems. It’s in the middle of nowhere. There is no golf anywhere close by and the nearest gentleman’s club even further. We will have a boat and enough beer to flood a small village, so maybe we’re overthinking things. The question is how to spend the weekend/what can we do preemptively to fill 2-3 days on the lake in a very off-the-beaten-path location? Just a bunch of rookies looking to the Jack Nicklaus of bachelor parties for some guidance.

Pretty new to the site, but am a huge fan of what PGP/TB are putting out there. Please keep it up, the community is so awesome and so are y’all.


Thank you very much for the kind words. The PGP community is very awesome, I agree.

You are over-thinking things. There are bachelor party destinations that set up nicely for golf (Scottsdale, South Carolina, etc.), gambling and strippers (Vegas, New Orleans, Lake Charles), beachy stuff (Gulf Shores, the Florida gulf coast, anywhere in Mexico), or even skiing. There are also a few places where you can knock out multiple bachelor party to-dos. Lake Tahoe, for example, has skiing and gambling. Any major city will provide titters and places to golf.

You just have to choose your destination based on what you want out of it. A lake house in a remote area will be a ton of fun, but it’s likely just going to be a few days of getting annihilated at the lake with your best friends, and there is absolutely nothing wrong with that.

Hey Dillon,
Question for ya, one of my good buddies (who I didn’t go to college with) just left for the navy and started hanging out/kinda dating my best gal friend from college right before he left and they plan to keep talking. My navy buddy is as solid of a guy as you can find and fairly normal but this is literally the closest he’s come to ever having a girlfriend. Gal friend and I hooked up a few times in college but nothing too serious (no sex). She and I are literally the only two people who know that this happened. Do I tell my buddy about it or not? He’s low key sensitive about this stuff and like I said he’s never had anything close to a real relationship. Plus telling him that right as he leaves for the Navy seems kinda fucked up. Also it’s been about a year and a half/two years since the hookups happened.

Thanks, you have permission to use this in the mailbag.

The first thing is you have to know that you’ve done nothing wrong. You hooked up with a girl a long time who your friend later on started talking to.

Since there was no sex, I don’t think you need to tell him yet. And you probably shouldn’t tell him at all UNTIL they start to get serious. If they are trending toward exclusive boyfriend/girlfriend status, you should tell him with a “Look, I have something to tell you that isn’t a big deal at all” approach.

So Dillon,

I’m in my first semester back in school (MBA, hoping to get to Ruff’s deal closing levels one day) and Spring Break is on the horizon. It basically starts with the weekend of St. Patrick’s Day and goes through the following week. The GF and I are planning a Dallas/Austin trip to visit her brother at SMU and also see Austin. What are a few things I should plan on doing during the week in Austin?

Thanks in advance, I’ll hang up and listen.

Austin is a great city filled with young, attractive people and a lot to do. The bar scene here very well might be the best in the country, though. Yes I’ve been to Bourbon Street but Austin is so different and fits me better for what I like to get out of bar outings. Yes, there are lakes and the hill country and parks and natural spring-fed swimming holes here, but if you’re coming for just a short trip, spend your time on West 6th, 5th, 4th, and Rainey Street for day-drinking.

Dylan Cheverererererere,

I’ve got some serious questions for thee, in fact they number three.

First, what is your favorite kids show that you’ve grown to love while watching with the kiddo?

Second, who has been the worst coworker you’ve ever worked with and why, either at grandex or in past careers)?

Third, what would be your go to walk-up song for a meeting you’re about to knock out of the park?

1) Definitely, absolutely, without a doubt it is Thomas and Friends.

I love that damn show. I get into the characters and the storylines like I’m a four-year-old. That Percy is such a little bitch, isn’t he? I’m so ready for his train balls to finally drop. Thomas is a cheeky little bastard and Emily is the really hot friend who keeps everyone in the friend zone. I need Thomas to make a move on that stat.

I can’t say that I respect the way Sir Topham Hatt does business, though. I mean it’s clear the guy runs a thriving rail line, but he lets his engines run amok all over Sodor and doesn’t come down on them like he should. They’re always disobeying orders and getting into trouble because of it, costing Topham Hatt money. Plus, whenever they run out of work to do, they all just go chuffing back and forth across the island to “play” with their friends while burning through so much coal. Just so many inefficiencies.

Sir Topham Hatt doesn’t exactly run a tight operation is all I’m saying.

2) I don’t think it’s right to answer this one.

3) “Who Am I (What’s My Name)?” by Snoop Dogg

Hi Dillon,

I’ve got a coworker who greets me with “what do you say?” or “what’s the word?” when making office small talk. How the hell do I answer that? It catches me off guard every time.

Now that I’m thinking about it more, it’s sneakily a decent power move. Throws people out of their loop. I might start using it.

If you’ve got any advice, it would be greatly appreciated.



It’s not all that similar but this question makes me think of Kramer getting several different greetings at the bank after they offer $100 to customers if they aren’t greeted with a “hello.”

I’ve actually had “what’s the word?” in my repertoire before. It think it’s totally acceptable to deviate from the standard greetings. Separate yourself from the pack, man. Personal Branding 101. Do you want your brand to be “Hi, how are you?” or something unique and off-the-wall? I don’t think it’s a sneaky power move, just a calculated branding play.


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. 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:

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