Mailbag: At What Age To Live Alone, Considering Dropping Out Of College, And Other Real Life Shit


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

Debate among old classmates as we have each gone down different paths in life and somehow I am the outcast in this debate in the entire fraternity who have taken paths One or Two.

Path One: Age 28 has never lived alone…parents house, college, then back to parents house.

Path Two: Age 28 has also never lived alone…parents house, college, shared house after college, then moved in with girlfriend so they can share a bougie one bedroom. Also the most common path of my friends who think they are “killing it” in their apartment they can barely breathe in with two people and a dog, welcome to New York.

Path Three: Age 28 yours truly…parents house, college, the same shared house after college and now my own apartment.

How am I the lepper in this because I can financially live on my own without my college friends, my parents or a rushed relationship to split rent with? I am going insane hearing them.

Path one people…yikes. I understand the job market can be tough in some places, but damn. I can’t imagine being a grown ass 28-year-old and living with Mom and Dad. I don’t judge, but path one people, make moves. You’ll be a lot happier.

Path two is a pretty popular one. In this scenario, I think significant other and friend/friends are interchangeable. Splitting rent is a good way to stretch your income out, especially if you want to live in a dope ass area.

Path three is a fine path, and 28 is a nice target age to be financially independent enough to live on your own. People are giving you a hard time for this? Why? Losers. You’re doing great. True story: I’m now living on my own for literally the first time in my life. There are the occasional “I wish someone else was here right now” moments of loneliness but mostly it’s just awesome.

Hi Dillon!

I was kind of hoping for some dating advice from an established and seemingly-successful guy. I just graduated from undergrad and moved back home. I’ve been single for almost 2 years, but I spent those two years very emotionally invested in a FWB that ended up going nowhere. Now that I’m home, where none of my friends live anymore, I find it super hard to meet guys (long work commute + no home friends = tired and can’t go to a bar alone on a weekend). I decided to meet up with this guy from Tinder, and he and I were both floored with how well it went. While we were out, he brought up a second date twice, and he texted me after to let him know when I’m free next, and also told me to text him any time. I guess my question is, how do I not appear over-eager? I’m 22 and he’s approximately 4 years older than me. He doesn’t seem like the kind of guy to text a lot, so I don’t want to be annoying by texting him a lot to chat even though I was really into him. I don’t want to screw this up, because it might have been the best date I’ve ever been on. How do I be chill about this and not drive him away?

A good rule of thumb is to play off his pace. If he takes three hours to respond, maybe don’t fire back right away. And if he’s a rapid fire texter, feel free to text more liberally.

I don’t know what it says about me, but I’m never scared away by overzealous texting. The way I see it, I want to be wanted, so if someone makes me feel wanted, I feel good about that. Now sure, there can be extremes. Don’t text him 500 times a day or show up to his work the day after your first date or anything crazy like that. But if you like the guy and want to talk to him, then talk to him. Don’t overthink too much. He should appreciate that you’re not playing games.

The girl I’ve been dating called me on the phone less than an hour after we exchanged numbers. Less than an hour! We talked for about 20 minutes and I think she gave me a brief rundown of her entire life during that call? I hate talking on the phone (she loves it) but she was all about it and showed initiative so I was like okay I guess we’re doing this shit.

Hi Dillon,

I’m a big fan of your mailbag, and I need some advice. My parents are currently hounding me about getting a graduate degree. However, when I try to explain to them that I don’t see the benefit they don’t understand that it’s not the right path for everybody. Plus, I’d like to be sure of what I want to do and enjoy the freedom before taking that kind of debt burden. What do you recommend I do?

Your life. Your call. And you’d be taking out a loan to pay for it yourself? Come on, Mom and Dad. This is one of those dilemmas that’s so black and white to me that my answer will always be something like “Just tell them how it’s going to be,” but I know it’s not always so simple. It really should be, though. They should respect your huge life decisions like this. Bottom line.

As parents, they’re going to encourage you to be your best self, as they should, but that encouragement should only take them so far. At the end of the day, it’s your move.

Hey Dillon,

Big fan of this series, it’s been cool watching questions grow from baseline topics to all varieties of deepness. My question for you involves marriage. I’m getting married in April and I’m curious what marriage advice you have. Things that change after marriage (we already live together), biggest discussions that happen, advice for navigating arguments, etc. Any thoughts would be much appreciated.

The underlying theme in a lot of my answers is communication. Communication goes a long way in a lot of situations and in a lot of relationships. That’s never truer than in a marriage. Holy shit please communicate with your spouse. About literally everything. Communicate well, and in depth. Be understood, and understand in return. My ex and I literally never fought, like literally never fought, and one of the reasons was our communication broke down at times. An issue would arise and we’d bury it or wait for the waters to calm again instead of dealing with them head on. Not good. Arguments are healthy. Have them. Be honest and open during them.

If you already live with your future wife/husband, then not a lot will change for you. You’ll just become as officially a couple as it gets, but the day-to-day doesn’t change. Keep the passion alive, please. Do that by, again, communicating about it.

Hey Dill,

This is a lot to break down.

I am not your primary demographic, but I dont want to talk to my parents about this cause my Dad would kill me if I suggested it.

I’m at a crossroads in life. I’m 20 years old and starting my junior year in college. I’m in the petroleum engineering program at TTU and have a 3.8 GPA right now.

But, it is incredibly stressful. My parents have been unable to help me through college so I’ve been working refinery labor jobs every summer after HS. While working as an RA and in fast food during school to pay for college and eat.

It has been taking its toll. School sucks for me right now. I go to class, the gym, study, and work. That’s it. My social life is almost totally nonexistent, maybe once in a few weeks I go to a party with my good buddies and get hammered but that’s it. Overall it’s really shitty and really stressful.

During the summers I work refinery shutdowns which are 13 days on 1 day off for 12 hours a day. The thing is, I’m not stressed at all. The work is hard but, I’m so tired I get really good sleep and the paychecks are incredible. The downside is that these jobs are always in bumfuck nowhere and so I have no social life during the summers aswell.

This semester for sure I’m going to decide whether I keep going to school or drop out and do the labor. If I drop out and keep working I could easily make 100k a year. Whereas some PE’s I know make north of 200k.

I don’t care so much about the money but my Dad has always wanted for me to go to college and make a lot of money for myself. And if I do drop out I would be a lot more alone than I am right now. Only 3 of my best friends who are going to school with me know that I’m really struggling. And they tell me to, “just weigh it out, and fucking do it.” This is definitely the most difficult decision of my life up to this point and I would like an outsiders perspective.

Thanks for reading this far and any thoughts y’all could pass on would be nice.

Man, you really should finish school. Get that degree. You’ve made it this far and, while I understand you’re really stressed out and spread too thin, you’re killing it in school and it’s setting you up for a really nice future.

I PROMISE you’ll regret dropping out now. I know your refinery job pays you well and eases your stress that comes with school, but the opportunities for you after you get that paper are far greater. And it’s not just about the money; it’s quality of life, too. Don’t do it for your old man, though. Do it for you. Stick it out for two more years, then the world is your oyster.

I’ll try to keep this quick:

High School football season is back. I haven’t been to a HS football game since my alma mater and I got knocked out of the state semifinals game almost 10 years ago. I went to college, then grad school, and now I’m back to my small-medium size home town. I have a professional career now so I don’t want to look like a goober, but I found my old letterman’s jacket and I would like an excuse to wear my most expensive article of clothing.

Am I okay as a mid-late 20 year old man wearing my jacket? I feel like this is maybe an easy “yes” down south, but where I’m from I could see a good chance at getting roasted from friends. Details worth noting: it still fits great, and is highly decorated. What’s your call?


Jack Et Guy

P.S. You have an official football throw-off next time I’m in Austin.

Speaking as a graduate from a central Texas high school, I would roast you off the face of the planet if you showed up to anything wearing your letterman jacket from high school. I wouldn’t stop until you cried, I’d end our friendship, and I’d do what I could to publicly humiliate you.

In Touching Base’s new segment, “Was That The Move?” the consensus among the three of us would undoubtedly be that no, it was not the move.


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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