Mailbag: Golf Polos In Bars, Older Women, Dating Advice, And Asshole Virgins


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


What’s your take on wearing golf shirts out to restaurants and bars? And not like after you’ve played a round. One of my more fashion conscience coworkers claims golf shirts are for the course, cotton is for everything else. I say as long as it looks good and fits, you’re good to go.

PS. Much apologies if this has been covered on Touching Base. I’ve got a few episodes to catch up on.

Grandex’s fashion guru, Barrett Dudley, will cringe at this but I think wearing a golf polo to the bar is okay as long as the sun is up. Like in a happy hour situation only. Or a late Sunday morning brunch after a night of drinking. If you’re going out-out, like dinner and bar hopping, then wear a real shirt.

Unlike Barrett, though, I tend to take the “I like to present myself as someone who takes pride in my appearance, but also look like I don’t care too much” stance on apparel. It was necessary to disclose that.

Hey Dillon,

I’m a 23 year old male grad student interning this summer in the city near where I grew up and staying at my parents’ house in the ‘burbs. This past Saturday evening, I was at a bar in the city with a friend and his girlfriend. While waiting on them to get their drinks, a girl approached me and asked if I’m single. After I went to buy her a drink, we talked for awhile and she told me that she’s been at her current job for 9 years. I thought I misheard her and didn’t think anything of it. Before we parted ways, she put her number in my phone and said she hoped to see me again soon. After a bit of research, I found out that she’s 8 years my senior. We texted back and forth a little the next day, but didn’t really get anywhere.

What’s my play here? I’ve never pursued a girl even close to this much older than me before. Should I call her later this week and ask to get dinner and/or drinks? Also, is my current living situation a deal breaker?

Your current living situation is likely a bigger issue for her than your age is. Probably a deal breaker, yeah. She’s 31. She’s a woman. She has her own place, is probably looking for someone who’s established, and is probably more looking for someone to settle down with than have a summer fling with.

I said probably, though. Maybe she’s into your whole situation. Shooters shoot, so take your shot.

Hey Dillon,

I need some relationship advice. I have been dating this guy for 4 years. We met in college and have been long distance for 2 years due to him being in the Navy. Since graduation we’ve been getting by on a plan that in 5 years he would leave the Navy and we could be more or less normal.

He has been deployed for almost 6 months and is coming home soon but I’m afraid we have both changed a lot in the last 2 years. He also recently decided that maybe he wants to stay in longer and that’s led us to wonder if we want different things in life.

Now I’m scared to buy a plane ticket to fly across the country when he gets back. I feel horrible about that. I should be excited. I just don’t know what to do. I’m worried that if we stay together we may be unhappy but I’m worried that it’s been so long that I won’t find anyone else. I’ve been living at home saving money for the house I thought we’d buy together and I’ve let me social life die. What should I do?

So many of these relationship questions get the same answer from me and makes me feel like I have a pessimistic outlook on things, like with the girl last week who had “zero chemistry” with her boyfriend. It’s just the nature of your questions, though. It seems that many of you KNOW what you should do and you simply need to hear it from a neutral third party. I get that. I’ll be your guy.

“Now I’m scared to buy a plane ticket to fly across the country when he gets back. I feel horrible about that. I should be excited.”

This part says it all. I don’t feel great saying this about a member of our armed forces, but you don’t seem to be very into him. You know what you should do.

“I’m worried that if we stay together we may be unhappy but I’m worried that it’s been so long that I won’t find anyone else.”

I totally understand this mentality (I’m currently going through it myself), but it’s never too late to make a move. Really. Believe it.

Dorn man do I have a situation for you.

I’m the 21 year old that asked about the gf with the alcohol situation. So I brought up that she should at least pay for half and she went BATSHIT crazy. She started screaming and punching me wherever she could basically caused a scene in public. She then proceeded to get a guy I went to high school with so drunk that she fucked him and he had no idea. (I was working late for my internship so I couldn’t go). So my question should I do anything in retaliation (her best friend is a smokeshow) or should I just let her psycho ass go and move on with my life?

Dude. You need to stay as far away from this crazy chick as possible. Do not retaliate against crazy. She’ll just up the crazy ante. Yikes.

“She then proceeded to get a guy I went to high school with so drunk that she fucked him and he had no idea.”

Yeah man that’s called rape.


I know postgrad problems is a website for college graduates but, even though I haven’t even graduated high school, I come seeking your wisdom as the question at hand is universal. To put it bluntly, I can’t get laid. In fact, I haven’t even hooked up with a girl. The polar opposite of Jared from Silicon Valley, I don’t fuck and I have no idea why. I know this is cliche, but I genuinely am a very good looking guy. On top of this, I make great grades with relative ease, my dad is a multimillionaire, I have an incredible sense of humor, and I can have a good time without being a douche about it. Why the fuck can’t I get some action? I just always find myself being the beta male even though I have everything going for me and my penis desperately needs to be in and around the mouth of a member of the fairer sex. I almost feel like my sense of humor makes me a novelty item but I just don’t know. How can I turn this ship around? Please Dorn, you’re my only hope. Well, you and jungle juice.


Your neighborhood misogynist

Your name (which I omitted) looks familiar. Are you the same kid who used to harass me constantly on all three forms of social media that I use? Are you the kid I had to block on Twitter, Instagram, and Snapchat because you’d constantly (daily) say disgusting things about my mom and call me a pussy and say I was scared of you? Didn’t I also block your friends’ accounts because you’d use them to circumvent the blocks on your accounts so you could continue talking shit and saying heinous things to me?

Maybe you’re still a virgin because you’re a little asshole and no one likes you.


This is one of those ‘tell me if I’m being a douchebag’ situations. I met this guy back in February and we’ve been hanging out on a semi-regular basis aka whenever we have some time in our busy lives. At first, it was just sex and we were both totally cool with that. Then I started developing feelings, but he essentially shut that down one night when we were both way too drunk for our own good.

After that is when things started getting weird…he wanted to know what I was doing all the time, he would get annoyed if I didn’t respond to texts right away and when I told him I was taking a trip home he asked if he could come with (I live in Europe and will be traveling back to the good ol’ USA for a visit), so its not something I took lightly.

So I started hinting that maybe we shouldn’t hang out so much anymore, and I finally ended up texting him that I’ll be on a long vacation and don’t really see it going anywhere. His follow up text was about getting as much time together before I leave. So, am I a total douchebag if I don’t respond? As a guy, have I not made my stance clear enough/ maybe I’m too subtle? I ghosted someone once and I felt terrible about it (still do), so I have a no ghosting policy, but Im not really sure what else to do.

So you got feelings and he wasn’t reciprocating, then it flipped and he got feelings when you weren’t into it? That’s odd. I get the feeling you’re not telling me the whole story here. Oh well. Not sure it matters that much.

You’re going on four months of dating this guy. Ghosting is always the wrong way to handle things, but ghosting after four months of dating makes you a total asshole. Respond to him and be blunt enough to ensure he gets it. It’s not fun to tell someone you’re not into them, but it will always be beneficial to that person in the long run.

I really just want to tell you I have a hook up at barton creek and I would love to take you out there and kick your ass.

I’m on record saying I will play golf with anyone, any time as long as you pick up the tab. If it’s down the street at Barton Creek, fine. That’s easy. If it’s Pebble Beach, that will set you back more than just green fees. I need you to pay for travel, lodging, and a meal stipend, as well. I won’t duck anyone.


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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