Mailbag: Dating Someone Younger, Sleeping Around After A Divorce, And Your Ex Moving Into Your Building


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

Hey Dillon,

I’m a 47 year old man dating a really cool smoke shop of a 30 year old chick for over a year. Now I know what you may be thinking, but no she’s not a gold digger — she’s got her own dough and frankly I’m not rich.

But anyway I’m quite older and back in my day we didn’t text 24 hours a day, and she does. If I don’t text her back like within 3 minutes I get the “hellooooo?” and god forbid it take more than an hour because that must mean I’m cheating on her. Even when I’m on the damn golf course.

Also, her go-to is to FaceTime rather than call, but in public places I think it’s rude to answer so I red dot her and again her assumption is naturally I must be with a chick. (I’m no player but I admit I am a flirt, and making friends with women comes naturally to me).

I adore this girl but honestly it’s exhausting to always be checking my phone and pecking out replies all day long. Talking with her about it has gone nowhere. What to do?

Congrats on landing a really cool smoke shop of 30-year-old chick.

So “back in your day,” texting wasn’t a thing. You picked up the phone and called people. That’s ancient. Everyone out here under 35 texts nonstop. That’s the way we communicate now. Talking on the phone is weird and outdated. If you’re going to date someone from the texting generation, you probably have to reach some kind of communication compromise and adapt.

Now, this one sounds pretty clingy. If the three minutes until the “hellooooo?” text thing isn’t an exaggeration, she needs to chill out. That’s stupid behavior. There are also some apparent trust issues on her end, most likely on account of you being an admitted flirt. I’m also going to go out on a limb and say you two aren’t communicating well. Make communication a priority. Talking shit out to the point where each of you understands where the other is coming from goes a long way.

Hi Dillon,

It seems like there’s another question about Austin every week, but I’m pretty sure this one hasn’t been asked yet so I’ll give it a shot. Anyway, I’ll be starting grad school at UT soon and moving from out of state. I won’t know anyone, so I’d like to live somewhere I can avoid undergrads/families and meet new people. Where is the best place for a young professional or grad student to live in Austin? I come from an infamous PAC-12 school, so I think I have some pretty high expectations of a social scene and I’d like to live in the center of the action. I’ve heard good things about Rainey and Sixth Street (and have been advised to stay west of Congress), but I’m not sure if it’s ideal to actually live in these areas. Sorry to be another west-coaster ruining Austin, but thanks in advance for your insight.

This one is tough to answer without a price range. You’re going to grad school so I assume you’re not flush with cash, but the areas you mention are some of the most expensive in an already very expensive city in which to live.

Rainey Street is a really fun and active place to live, but it’s expensive. Not many people live on 6th Street, but the area just south of it is a happening spot. The Seaholm District, for example, is right in the heart of the action. Again, though, it’s really pricey. I’m about to live on South Lamar, just south of downtown. I love the area. It’s surrounded by so much to do and it’s full on young professional types. While still expensive, it’s not as high as it is north of the river in downtown. The farther south you go, the more affordable it gets.


I recently came across your podcast where you discussed your divorce. I’m sorry to hear you’re going through that. Thanks for your candor in sharing. I recently went through a divorce myself after almost 5 years of marriage. I’m 30 and struggling with getting back into the singles social scene.

I have no idea what the hell to do when it comes to girls anymore. I’m a good looking guy and never had a problem getting laid or dating before I was married. The first time a girl approached me at a bar after I was separated, though, I freaked the fuck out. It was bad. Like, I don’t think she’d even acknowledge me if we passed each other on the street I acted so weird.

I’m not looking to jump into a relationship, but you know, girls are nice. Is it sleazy to go out looking to get laid at this point? I’m not going after 18 year olds or anything, but I just feel weird about the whole idea. Is there such a thing as casual dating/hooking up for people in our situation? Maybe at this point it’s only legit dinner dates. I’m cool with that. I even kind of like that idea. Just not sure what to expect and where to set my expectations.

Thanks for the guidance.

Welcome to this weird world of “getting back out there” after a marriage. It has its highs and lows and is an overall trying and difficult experience, but this phase is temporary.

I don’t think it’s sleazy to want to go out looking to hook up with women. After all, you’re not ready to be committed to someone quite yet. That makes sense. You shouldn’t commit to anyone for a while probably. That’s where I am still. Take the time to get to know yourself better as a newly single person and ease back into dating when you’re ready. 30 is young. You’re young. You have all the time in the world. You’ll find your stride.

Dinner dates, just drinks, casual dating, hookups, wild sex — they’re all on the table but you should be upfront about what it is you’re looking for.

Hey Dorn really enjoy your mailbag it really makes my work day fly by, anyways I had a question about friends paying you back.

1) We went on a golf trip and he owes me $150 and hasn’t paid me back. Do you think I should drop him as a friend or how would you handle this? He’s one of my best friends.
2) Also if it was your last summer as a college student is there anything you wish you could go back and do?
3) Additionally how do you feel about guys with tattoos do you like them or nah?
4) Lastly how would you rank your favorite SEC schools to visit?

1) You don’t drop a best friend over $150, but you do put him on suspension until he pays up. He’s being a shitty friend, so tell him that.

2) Yeah I’d go back and be single.

3) Tattoos are so common these days that I barely notice them anymore. I’m not a tattoo guy but they don’t “bother” me. Now, I will say there are some people out there with truly awful tats. Just terrible and embarrassing. You asked me about guys with tats but I’ll give you an answer on girls with tats, too. I’m less attracted to a girl with aggressive ink. A little one here or there in awesome/cool/subtle/sexy places can be hot, but if you have a calf tat, or a full sleeve, or just a big one somewhere, I’m not going to be into you.

4) UGA, Ole Miss, LSU, Vandy — in that order. I have no desire to visit any others.


My ex girlfriend from college, who has been working in the same midwestern city as me for over a year, just moved into my apartment complex this past weekend 2 floors below me. PGP. I ran into her the other day and she said to me what a crazy coincidence it was. She proceeded to text me the following night that we should go out for casual drinks and just “catch up,” which I have already politely declined because of the current relationship I am in with a very nice lady.

I know my girlfriend (who lives on the other side of the city) is not going to happy hearing about my ex living near me. I’m planning to tell her as soon as possible rather than have her find out when she’s here, but I don’t know exactly how to go about that.

I have 6 months left on my lease, and the apartment location is great for me, it’s in a fun part of town and close to work, so I don’t really want to deal with figuring out how to move right now because of this. And I don’t blame my ex for wanting to live here since it attracts a lot of other yuppie millenials. How should I go about handling this?

You’re in trouble. You just described your girlfriend as “a very nice lady.” Translation: “Yeah she’s okay.”

You also haven’t told your very nice lady about your new neighbor friend. Hmmm I wonder why. You don’t know how, you say. What do you mean? How about a “Yo, guess who moved into my building” text? It’s that easy. You’re keeping it from her, homie. I see you.

Prediction: Your current relationship doesn’t make it three more months. You’re clearly still into your ex or you wouldn’t have emailed me about this. It would be a non issue if you weren’t. Visions of late night, drunken elevator rides down two floors are running through your mind, aren’t they?

You handle it by either telling your ex you won’t be hanging out with her or by telling your girlfriend what the truth is.


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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