Mailbag: When Your Friend Is Dating A Shitbag, Best Chance At A Post-Wedding Hookup, And Pro Shop Purchasing


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

Hey Dillon,

Hoping to get your advice and advice of fellow PGP’ers. What, if anything, is a good way to convince a friend that he/she is dating the wrong person and the cycle of breaking up/making up must end? Is there anything that can be done, or is this a realization that one has to come to completely on their own?

Short backstory is that my roommate, who is also my friend of 10+ years, has been dating this guy whom she’s convinced is “the one” but he’s actually “the worst.” All of the typical stuff: controlling, manipulative, outright mean, forces her to be isolated from her friends, accuses her of cheating (even though she hardly ever leaves his sight), forces her to share her location on iPhone, etc. He redeems himself from time to time by doing something nice, but the bad largely outweighs the good.

I would normally just do my best to ignore all of this but, since it’s my roommate, it’s challenging to pretend it’s not happening. I tried the “tough love” approach about a year ago (“he sucks, you need to stop”), which caused her to only fall deeper into his traps. Plus, I don’t want her to feel like she can’t talk to me if I’m too harsh with her. But, she recently mentioned that the two of them had discussed marriage (?!?!), so I feel like something has to be done now.

Is there a right way to convince someone that they really need to end a relationship for their own good? Or, is she a grownup and I have to let her make her own mistakes? For reference, all parties are in their late 20s.

This is absolutely a realization she will have to make on her own. You can, and you should, express your thoughts to her about the guy as long as you have her best interests in mind. You’ve done that. You’ve done your job. Now your job is to let her figure the rest out on her own. It sucks, and it’s hard, but it’s what you have to do.

Trying to tell someone how to feel or how to think is a losing endeavor every time. She will most likely grow to resent you if you’re persistent about it. I think the more people who share their negative thoughts about this asshole helps, but all the advice in the world will only take her so far. It has to be her realization.


I just finished a podcast on Super-Recognizers and how their skills translate to cool jobs. You’ve done good work for Grandex over the years, but do you ever feel like you missed your calling as a CIA agent or local politician with your ability to spot a face and never forget it?

– Someone who forgets most faces.

Thank you for bringing attention to my very rare and amazing superpower.

First of all, I have a very cool job already. I love what I do and have no desire to seek employment elsewhere, even though this incredible ability I have is of no use to me in my current role. Am I not fulfilling my societal duties? What if Superman was in sales? Or if he was a gamer nerd who never left the couch? What an absolute waste of abilities that would be.

I have wondered on occasion how my being a super-recognizer would land me a really sweet gig with the CIA. Taking down the world’s high profile criminals and all that. I don’t know how this power would actually translate to a different, cooler job, but I’m happy where I am. At the end of the day, it’s fun to be like this, and that’s enough for me.


Hey man, I’ve noticed you give out a lot of sound advice so I’m looking for some help. My brother is getting married soon so I was curious on the protocol of hooking up with someone at a wedding like that. I’m torn because I am not in a relationship so I would have to either find a plus one or hook up with a mutual friend of either my brothers or the brides. I’m thinking maybe this is a type of wedding you would sit out of the hookup game, what do you think?

All you hornballs out there looking at every occasion as an opportunity to get laid. I love it. Ways to pick up girls at the grocery store, at the gym, at baby showers — it doesn’t matter. It’s always time for sex.

Your best chance at hooking up after this wedding is probably to take a date. You arrive together, you drink adult beverages, then you leave together. It’s a recipe for sex. And as the brother of the groom, you’re allowed a plus one even though you’re not dating anyone currently. So shoot your shot. I bet you already have someone in mind to take.

Hey Dorno,

I’m lucky enough to be traveling this fall to both Jacksonville and San Diego, and I’ve managed to lock in plans to play the Sawgrass Stadium Course and Torrey Pines North (humble brag). These are likely the only times I’ll get to play these tracks, and would like to have something nice as takeaways from each. Should I go with the standard dri fit polo or hat with club logo from the pro shop, or should I grab a flag, ball marker, or one of the other miscellaneous items they have for sale? Would love your opinion along with the commenters.

I’m big on apparel. You get the most use out of it. You wear it around, people ask you if you’ve played there, you get to talk about your experience, etc. It’s good stuff, and it shows you get around. What are you going to do with a flag? How many uses will you get out of a ball marker? How many people will see your Torrey Pines coffee mug that you’ll inevitably lose or break the next time you move?

Scoop a dri-fit and a cap and call it a day.

​Sup Dill,

Two part question for ya. So I recently moved to a new city and started a new job in construction management. Got a few old fraternity brahs ​in the area, but all kinda spread out. Wondering what you suggest for a new postgrad to meet friends? Secondly, as I mentioned, I work in construction. At work I wear dad jeans, tucked in polo, and a phone on the contractor belt clip. Kinda look like a fool. Whats my play here, do I take the extra hassle to change before I go out to bars/dates or do I full on embrace this look and wear it 24/7?

Stay frosty,

I’m including this question because this was the exact work attire I used to wear every day, and it brings me back. I used to work for a small construction company here in Austin and I wore white-washed Wranglers, Justin boots, tucked in polo, a hat, and a Nextel attached to my belt via belt clip. FUCK.

What an absolutely atrocious outfit. Dude, listen to me: You cannot wear this in any bar outing, dinner, hangout, or social gathering of any kind, whatsoever. It’s for work. Leave it at work.

Hey Dillon,

First off, gotta say, I appreciate the content. I’ve been an on again off again reader of TFM since way back in 2012 and PGP more recently, and I’ve gotta say, my morning shits wouldn’t be the same without them.

Anyways, my question. I’m 23 and after working and going to school part time in order to pay tuition I’m pulling the trigger and heading back to a four year university to finish my degree. The school I’ll be attending is only about 10,000 people, well known for being a party school, and has a fairly subdued Greek life. I have every intention of partying and enjoying myself, but my academics have to come first this late in the game. Is it worth it to join a fraternity? Am I too old? What’s your take on people going back to school after a certain age?

I don’t know the likelihood of this making it on the site, but I’d certainly love to hear your opinions.


I wouldn’t join a fraternity at 23 years old. I probably wouldn’t join a fraternity at 20 years old. At 23, I’d be thinking about getting my degree first, lining up job prospects second, then having a social life third. Not that having fun isn’t important, but it’s just different when everyone around you had a five-year head start. Priorities change over time.

You can still have a blast in college without joining Greek life, which you say is “subdued” anyway.


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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