Mailbag: Dream Vacays, Smoking Heaters, And Girls With Small Dogs


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

Hey Dillon,

I thought this would be a good question/hypothetical for a mailbag or touching base topic.

Out of college I got a job at a tech company with a interesting perk, every 5 years, in addition to normal vacation days, you get a 4 week paid vacation to visit a country you haven’t been to. They’ll pay airfare for you and one other person (up to $2,000 per person, coach only) plus $300 per day you spend in a country you haven’t been to, and it all has to be taken at once. I’m coming up on my 5 year anniversary this summer and am torn on what to do. The two main schools of thought. You could fly to a random island and relax for a month doing island stuff, Bora Bora looks pretty sweet but could it get old after 4 weeks. The other option is to use it as an opportunity to “immerse yourself in a different culture”, spending a month bouncing around Italy could be a good story but could also be exhausting. The third option is take a month off and spend it at home or driving around the US, but that doesn’t take full advantage of the perk since you don’t get any extra money.

What should I do? What would you and the Grandex guys do or recommend?


First of all, your company is awesome for offering you this.

This is a tough one. I see your point about getting tired of sitting still on a beach for four weeks. After about five days of that I’m ready for a new scene.

I’d go with the cultural experience of Europe. I’m guessing you don’t have to stay in one country the entire four weeks, right? I’d drink and eat my way across western Europe — Belgium, France, Italy, Germany, Switzerland, Spain. Maybe even time it so you can catch the The Open Championship? I’d cover some serious ground. Immerse the fuck out of yourself. Look into Thailand, too. I hear good things.

So I’m pretty sure over the past three years I’ve given nearly every dating platform a run, however, I’ve yet to make it past a second date with anyone. I don’t think I’m ugly, I work out at least three days a week, eat healthy (for the most part), and have a good, well respected job. Unfortunately, I just can’t catch a break when it comes to dating. I also don’t meet very many new people so meeting someone IRL might be even more of a struggle than online. Help, I’m screwed.

Note: This question is from a girl.

With this very limited information, there’s no way I can give you a good answer. But if you’re not ugly, in good shape, have a good job, and still can’t get past date two, it’s possible you have an insufferable personality. My guess is that’s not accurate, though, and you simply need to find ways to meet more guys. We’re not all destined to get along. Hop on Bumble and you’ll find someone.


Let’s talk burning heaters.

This is really the epitome of a post-grad problem, IMO.
Step 1. You go to college
Step 2. You drink too much, and you’re regularly around people who smoke darts
Step 3. You start bumming cigs
Step 4. (optional, but common) You develop a mild smoking habit. You probably aren’t smoking fifteen per day, but you always have a pack laying around. You smoke when you drink, when you play golf, when you’re on 20mg of Adderall in the library, etc.
Step 5. You graduate.

Step 5 is where things get interesting. When and where is it appropriate to burn one down in public? It seems to me that pretty much everyone in the foregoing position realizes smoking is not a good habit to carry through life, but anybody that had a good time in college knows the occasional Marlboro 27 with your buddy can go a long way.

I’m in law school, which can be a rather uptight crowd, yet I don’t feel bad in the slightest about stepping outside the bar and enjoying a sample of whatever the undergrads outside are chiefing-down. However, I’m currently overcome with anxiety at the thought of curbing my Adderall high with a cigarette outside the library. I’m not sure my reputation can take the hit of being spotted by a classmate (i.e. attractive girl).

Keep up the good work. Big fan of the HPO movement.

Great topic. Great question.

I’m outspoken about my propensity to burn down when I’m a few drinks deep. I have some rules, though. The first, of which, is a big one.

1. Never, under any circumstances, do I smoke a cigarette while sober. I have a three drink threshold before I allow myself to smoke a heater. The school of thought here is that if I never allow myself to smoke without drinking, I will never want one while I’m not. So far, this has worked for me.
2. Never smoke alone. Burners are for social settings only. Furthermore, never smoke alone while at a social gathering. Want to step outside the bar and burn one? Cool, but find a Burner Buddy™ to go with you so you’re not the guy fiending so badly that you have to burn alone. That’s not the look.
3. Your limit is three a night.

If you need to smoke a ciggy to calm your nerves while studying or whatever, man just be careful. That’s how you become a real smoker. Don’t worry about how it looks to others. Worry about becoming a real, regular smoker. It’s an awful, disgusting habit.

Hey Dillon

This is probably one you’ve gotten before but here goes! I met a guy on Saturday night, he’s a friend of a friend, and one thing lead to another… Shameless making out and he got my number. He messaged me on Sunday and we’ve been in regular communication since then. He also mentioned a couple of times on the night about seeing me again so my question is this: do I take the initiative and suggest a meet up, or leave it to him? I normally wouldn’t hesitate to go for it but I’m sick of being single and don’t want to fuck this up.

Really appreciate your help.


Ask this dude out. It’s not 1950 anymore. Ladies are out here asking guys out. It’s normal in 2017. He might be one of these guys who isn’t super confident and will hesitate to make the move and ask you out. Ask him and you’ll know if he wants to hang or not. It’s no big deal. Promise. If he’s somehow intimidated by this move or just not into it, he’s soft.

Hi Dill,

1st off, does anyone call you Dill? If not, you should own it.

2nd, I’ve got a pretty solid iron game and my driver isn’t bad (hitting the fairway about 75% of the time, which I’ll take). I suffer around the green. If I don’t get on in regulation, I’m boned. I’ve tripled chipped before. It’s hideous. Any advice on how to improve my short game?

Dill, Dildo, Dill Pickle, yeah I’ve heard them all.

I have an absolutely atrocious short game. You’re simply asking the wrong guy.

Hey Dillon –

I’ve been casually seeing this girl for a couple weeks now. No clue where this relationship may or may not go. So far everything has been ok, except one thing; her fucking dog.
I hate her tiny dog. It basically is a cat that poops outside. I love dogs. I have a dog myself. My dog also hates this small dog. Her dog does nothing but yap and try to hump my dog. My dog is significantly larger and well trained. He just brushes off the humping and moves to another couch or whatever to try and get away from this little shit. This goes on non-stop whenever she brings this little yapper around.

Is this a deal breaker? Do I need to end whatever this relationship is now? Am I overreacting? I’d appreciate your input.



I totally feel you about tiny dogs. Well, I should first state that not all small dogs suck. There are some chill ass tiny dogs. The ones who don’t hop up on couches and jump all over you and yap and actually respond to commands — those are fine. Most of them are awful, though. MOST ARE AWFUL. Why anyone would willingly own a shitting, pissing, yapping, hyper ball of fur, I will never know.

I went on a date with this girl a few months ago who invited me back to her apartment. We sat on her couch with a glass of wine and just talked for a little bit. She had this tiny dog who was crawling all over me and licking my face and yapping its head off. She didn’t stop the entire hour I was there. I didn’t want to be rude and tell this girl, “Can you please get your fucking dog away from me?” so I let it happen. I’m over here trying to get to second base and her dog was getting to third with me. It was terrible.

I’m not saying it was a deal breaker — if she was someone I wanted to be with, I would have learned to live with the dog being around — but it was definitely a mark in “cons” column.


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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