Mailbag: Dating Your Friend’s Mom (!), Balling On A Budget, And A Girlfriend Who Won’t Reciprocate


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

Sup Mr. Chèvre,

I’ve got a unique predicament here for you, but first a quick background. After college I moved away to a city where I don’t know anyone. Ended up moving in with my friend’s mom there. The PGP commenter group lovingly refers to her as my mamí. Anyway, she is divorced and has a son. The dad is kind of a shit bag so the kid sees me as a friendly father figure. He’s headed off to college in AZ in a few weeks and decided two weeks ago to lock down a girl who’s going to be a senior in high school (aka not going to school with him out of state).

His mom asked how I felt about the situation and I told her I think he’s being an idiot for trying to date a girl at home while away at college. She asked if I could talk to him about it, so my question to you is this: what is the best way to approach this subject with him, and do I tell him he’s making the #1 mistake of going away to college or do I just softly warn him and let him figure it out on his own? Like I said, he’s going to school in AZ – noted hot girl mecca, so he’ll be able to do so much better. Let me know. Thanks and keep churning out top notch #content.

Sent from my iPhone 7+

I’ll get to your question in a minute but I’m having trouble digesting all of paragraph one. You graduated college and moved in with your friend’s mom in a different city? You said she has a son…yeah, your friend is her son, no? So this is another son, a younger one, and this one is going off to college. Correct?

I think I want to know the age difference between you and the mamí and how you came to know her. Also, how’s your friendship with her older son going? Not great? What a wild ride this is.

Yeah her youngest son is an idiot but he’ll figure it out. There are lots of 18-year-old idiots making this same mistake and they’re all going to figure it out. The first rush party he attends will be an eye-opening experience for him. Keep it real with him. Tell him he’s making a mistake that he will look back on with regret then step away and let him do this thing. The kid will be alright.

Then again, if you were four or five years older than me and giving my mom the business, I don’t think I’d respect anything you had to say to me.

Hey Dillon,

Long-time reader, first time writing in.

My live-in girlfriend of 2 years is moving out of our one-bedroom apartment. We’re donezo. Being nearly 25 now, I figure these next few years are prime-time for another (final?) round of sleeping around.

I’m pretty excited to get back into the game. I’m fairly new to the city (Baltimore), and it feels like I’ve a lot to explore yet.

As optimistic as I am, I’ve two obstacles:

1. Any game I had before? It’s been long-lost to too many lazy nights on the couch with the ex. I’m rusty as hell man.

2. I’ll be paying full rent instead of half. No big deal, but it does mean I’ll have to cut back on my lifestyle. No more getting drunk on $12 specialty mojitos (probably the worst part about this break-up), and probably fewer nights out with friends overall.

So, any advice on getting back into the game… and on a budget?

You’re asking a guy who has never really had any game to speak of. I’ve never been one to approach girls out in the wild, and I never will be. I just wasn’t wired for it. Practice, though. Repetition creates comfort. Line up some dates, have exactly one drink before you leave the house, and keep the convo moving. You’ll do fine.

I’m not great at balling on a budget, but look into happy hours. There’s no shame in scheduling a happy hour date. Also, avoid dinner until date two or even three. Drinks only will keep it cheaper until you learn if she’s worth the dinner investment or not. Movie and wine night at the crib, too. Cheap, fun, and ups your chance at hooking up.

Suh dude? Relatively new toucher touching base here. Curious as to your thoughts on the rope-tribal-necklace things all (most) of the guys were wearing on episode 1 of Bachelor in Paradise? Still noticed a few of the guys wearing them on episode 2 but they weren’t wearing them as much as they were episode 1. Could this be some indicator as to what their status is with the ladies on the show? Your thoughts?

If you didn’t notice that’s cool. Also, I’ll be foregoing promo code sock on my first manoutfitters purchase like that other guy bc I want you guys to stack paper.

Best regards,

Chris Mullen

As I understand it, those awful rope necklaces are actually microphones, or at least they conceal small microphones in them. Typically, their mics are attached to their shirts. You see the guys wearing these when they’re shirtless — at the pool, on the beach, just being shirtless douches, etc.

Someone correct me if I’m wrong.


Congrats to the homie on the new haircut. No better feelings than a fresh cut.

Is there any concern the homie might be too fresh for his age? I definitely want my guy to bully the loser kids starting day 1, but I’m worried that if he’s too far ahead of the curve, he might not have other homies to rock with.

I’ve been thinking about this question since it hit my inbox a couple days ago, and I cannot figure out how you know The Homie got a fresh cut. Snapchat? Did The Homie’s fresh new look make an appearance in my story? Someone help me.

I haven’t considered the bully angle, but The Homie is devastatingly handsome. DEVASTATINGLY handsome. Are you suggesting he might be so good looking that he’s bullied for it? I’m picturing a 5th grade George Clooney getting pinned against his locker for getting too much attention from the ladies. Man, bullying must have changed since my day. The uggo kids were always the ones left out of kickball and shit.

P.S. Bullying is a serious issue tbh. Come on, man. Don’t let your kid be a bully.

Sup Dorn,

I will be in Houston for a week at the end of August. I am in my mid twenties and from The North #TeamJon. I know you’re not from there, but others from Grandex are. My question is fairly general due to this being my first time visiting Texas. What is the appropriate attire for going out to the bars? I’m a big “nice pair of jeans or slacks” kind of guy, aka I skip leg day. This is something I can get away with up here in Michigan due to cooling temps at night, but will I be sweating excessively like Will is putting off his proposal? I don’t want to be unapproachable due looking like Chris Berman while he plays a round of golf. Also, any go to spots recommendations from you or the commenters? Also, sup to my future Bumble matches?

Dress like you’ll be in the most depressingly humid environment on the planet, because, from my experiences, that’s exactly what Houston is. Honestly, you’re fine sticking with your usual attire of jeans or slacks with a button down, as long as you’re wearing this well after the sun goes down. Yeah you’re going to sweat some, but there’s no escaping it in Houston, no matter what you’re wearing. Everyone and everything is sticky in that city. Daytime = shorts. Night = pants.


I am a big fan of the mailbag column and touching base. Since you are so good at giving relationship advice I figured I would run a question by you. I have been dating a girl for almost two months now and we hook up regularly. However she has never even hinted in the slightest about going down on me even to return the favor. How do I go about bringing this up? It is not a deal closer but it is nice on occasion.

I think you mean deal breaker, not closer. You’ve been listening to too much Touching Base.

What you have here is a selfish lover. You’re saying you go down on her and she still isn’t reciprocating? She’s a selfish lover. There are ways to bring it up without torpedoing yourself, but you have to be delicate. Maybe even joke about it. “I’m glad you enjoyed that. I wonder if you like it as much as I do.” Something like that, maybe?

Some girls just aren’t into it and won’t do it. True story. Good thing it’s not a deal closer for you.


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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