Mailbag: Sexual Unfulfillment, Water Cooler Talk, And A Million Dollar Secret


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


Huge fan of the mailbag, don’t disappoint me plz. My boyfriend is 15 years older than me. Sounds bad, but me, my friends and family love him. He’s very outgoing and an all-around great guy. To the point- sex used to be amazing but now it’s mediocre. Every day went to 2/week and I’m worried it will continue to progress this way. With busy work schedules and active social lives, I wonder if this is to be expected or abnormal. He thinks my expectations are too high, but in reality I just want to get laid on a regular basis (aka every day). His side or my side, please interject.

It would be helpful to know how long you two have been together. If the sexual intensity is fading after three months, yeah I’d be worried. Of course, it’s normal for sex to become less frequent and not as intense as you get deeper into the relationship — the theory of the seven-year itch is a real thing.

It would also be helpful to know how old this cat is. If you’re 32 and he’s 47, for example, his age could be a factor here. Slowed libido and low T. All that shit. If he’s older like that, daily sex could be a tall order for him. Two times a week is definitely on the more normal end of the spectrum for an established couple, however. Some guys would kill for that much sex.


Yesterday I overheard a guy in the office ask someone else how their weekend was solely for the chance to mention that he took the family out in an RV on Saturday.

This and your water cooler video had me thinking: Who is the worst guy at the water cooler right now? Is it Game of Thrones guy? Bachelorette guy? ‘Did you see the game’ guy? Did you hear _______ podcast guy?

Is there ever an appropriate topic in this spot?

GoT water cooler guy is a big one right now, but he’s about to be dethroned (I hate myself for this joke) by fantasy football water cooler guy. He will ask you about your fantasy team, not because he cares even 1% about your team, because he doesn’t, but solely so he can tell you about his team that you don’t care about.

“Did you see the game?” water cooler guy is high value member of your office social scene. Let that man do his thing.

Dear Dillon,

Let me give a little backstory before I start with the questions for a better understanding.
I grew up in a very conservative atmosphere growing up, my parents didn’t drink and I didn’t as well. I never went to parties and stuff and I “stayed out of trouble” I guess you could say. My friend groups were mostly conservative as well, even through college. I’ve only dated one girl and stop dating because I wasn’t getting married.

Well now I’m different and I want to go on dates and hopefully hookup eventually. But I have no clue on how to do that. Tinder/bumble doesn’t seem like it’s going to work because my profile pictures suck (hopefully I can get better pictures) and I think I’m shooting for people who may be considered “out of my league”. I would like to try to go to bars and try to pick up chicks there or even just hang out with friends but I have no experience going out and now since I’m out of college opportunities to meet others that go out is lacking.

I’m currently going to the gym as much as possible and I’m going to try to take dance lessons this fall, but other than that I don’t know what to do. Do I just go to the bar alone? Or what that be weird to not have a wingman/wing woman?

My initial thought is you have a bit of a confidence issue. You’ve been out of the game for, well, ever? Context clues tell me you were saving sex for marriage until you decided to live a more hedonistic lifestyle like most of us savages out here. It would make sense for you to be short on confidence at this point in your life, so don’t even worry about that.

You just need to get in the game. I don’t care how you do it — Bumble, Tinder, talk to girls at the gym, hitting the town — but you need to do it. Force yourself outside your comfort zone so that it’s eventually no longer outside your comfort zone. The gym will certainly help with your confidence, but immersing yourself in social settings is the key here. And no, don’t go to bars alone. That’s weird.


My best friend from high school is getting married in November and I’m thrilled for her. This past Sunday I was down at her house for a barbeque and the groom to be found himself about 3 beers too deep. Being the good pal that I am, I offered to drive him home. On the ride to his apartment, he drunkenly disclosed that he has a cool million in a savings account that he inherited from his grandfather- and my best friend has no idea. He wants to save the money for their retirement, and doesn’t want her to know because she would want to plug a huge chunk of it at her student loans and a house. I think he is wise for planning to save the money, but a million dollar secret is no way to start a marriage. So… WTF do I do? Should I keep my nose out of it or create a huge mess two months before their wedding?

You’re right. Keeping a secret like that is not a good foundation for a marriage. I think you need to have sober conversation with him and explain that A) he put you in a tough position by telling you his secret, and B) he needs to tell your girl. Like now.

On another note, sitting on a million dollars until retirement is LAME and probably not even the best use of that money. Hopefully he’s at least investing it wisely. I’m taking some of it and outright buying a house. Owning a piece of appreciating real estate that is your home base for years to come — that’s huge. No mortgage payments? That’s what I’m doing. Put the rest away or pay off those student loans or whatever. Sitting on a milly for the next 30 years, though? Come on.

P.S. When I read “On the ride to his apartment, he drunkenly disclosed that….” I thought this was going a much worse direction.

Sup Dillon,

I don’t know many people who have had experience with this so I figured I’d ask for your expertise (+ the PGP crowd).

I’m looking to go on a solo vacation in the next few months, most likely within the US seeing as how I’m balling on a (very tight) budget. I have a ton of places I’d love to visit, but I’m not sure if they’re ideal solo spots. Any location recommendations? I’m a 23 year old female so I’m also a bit nervous going out on my own. Any travel tips?

I’m including this question so the PGP crowd will chime in. I’ve never traveled alone but I’m pretty sure I’m going to next spring/summer. Possibly to Europe. So I’m curious what people will say.

Some of my favorite places I’ve been to in the US: San Diego, San Francisco, Napa Valley, Seattle, Charleston, Washington DC. Note: I’m not a New York City guy and I haven’t been to Chicago yet.

Hey Dillon,

Every college football season, my buddies and I take a trip somewhere in the country to watch a game and experience a college town that was different than ours. Recently, we went to LSU and Oregon. The problem we run into is that because we’re all Midwesterners and have been out of college for a few years, we don’t really have a great idea of what do on each campus before the game.

This year, we’re heading to the UT – Oklahoma State game. So my question is: What are the best things to do in Austin on game day? Bars? Tailgates? Food spots?

Thanks for the help. Hook ’em.

Head to Scholz Biergarten to start your Saturday. It’s a game day staple in Austin and it’s in the heart of the tailgating action. Then walk to the Grandex tailgate and enjoy free drinks with us. Details to come.


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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