Mailbag: Hating Your Engagement Ring, Chasing Tail To A New City, And Family Vacays


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


Need your impeccable wisdom, man. I’m at a bit of a crossroads in life right now. To make it as short as possible, I just graduated in May and I have an internship which lasts until August, and after August I have no idea what to do with my life. The most pressing reason being I just broke up with girlfriend of a little over a year. She just got a great job in a city about 9.5 hrs away from where I live, but we had been doing a long distance relationship for the entire time we were dating, and had planned on moving to the same city after I graduated. 9.5 hrs is just not realistic, and the relationship had been kinda rocky for a few months now. If I found a job in the same city as her we might get back together and would likely be happy, but I don’t want to take a job in her city unless I find a great opportunity which is probably not that likely, and she has told me the city she’s moving to kinda sucks. She is an amazing woman, though, and I still really want to be with her. That being said, I have lived in Nebraska for my whole life (23 years), never traveled, never done anything that cool. I also have always wanted to live in Colorado to be close to mountains, skiing, all that shit. So pretty much my question is…if you were in my shoes, would you try to find a job close to the woman of your dreams and hope things work out with her, say fuck it and save up some money for a couple months and just travel around Europe or somewhere by yourself for a month or 2, or just pick a city like Denver, FoCo, Boulder, and try to find a job you might enjoy out there. Any insight you can give me would be really appreciated, dude.


Confused AF

Do people really call Fort Collins “FoCo”? I now hate Fort Collins and I previously felt totally indifferent about it. “SoLa” is a name given to my new neighborhood since it’s on South Lamar Blvd., but I’ve yet to hear someone use it in real life. I’ll hate whoever does, though.

First of all, this girl is not the “woman of your dreams” or you wouldn’t be asking me all this. You don’t consider options B and C if option A is being with the “woman of your dreams.” You’re 23, man. You have so many girls to meet in your life still. I’m not saying she’s not awesome — I’m sure she is — but the simple fact that you’re considering living far away from her by choice means you can potentially foresee life without her by your side. Very telling.

Move to Denver. Move. To. Denver. A trip to Europe would be sick (your option B) but then it’s over and you’re poor and back at square one once you return. Go be independent in an awesome city where you can find a good job and go skiing and hit the bars and do outdoorsy shit and fire up the Bumble machine. Fuck that sounds awesome.

You have GOT to get out of Nebraska.

Dill Pickles,

How old is too old to go on a “family” vacation? I’m married. Been off the family payroll for 8 years now. My mom is headed to Hawaii for Christmas though. Is it weird if the wife and I go? Are we too old to bum off our parents for vacations?

Gracias Senor

Never. Never. NEVER.

You are never too old to let your folks pick up the tab on a lavish vacay. If they’re offering, you’re going. It’s just dinner on a bigger scale. You let your old man grab the check after dinner, don’t you? Parents love spoiling their kids, so as long as they have the means to do so, let them. There is no shame in it whatsoever. You’re going to Hawaii for Christmas.

Hey Dillon,

Long-time reader, first-time emailer. I have been dating seriously *the* most awesome guy for about 4 years now. His mom passed away when he was very young (like kindergarten young). Since then, dad has remarried and all is well. Obviously, I never met his mom, but just based on how great I think her son is, she must have been really wonderful. We’ve talked about getting engaged, but I know for certain he hasn’t bought a ring yet. I’ve wanted the same ring (cut, setting, band material, etc.) for as long as I can remember. Maybe I’m superficial, but I’ve dreamed about this ring. It’s THE ring. The amount of pins I have of it on Pinterest is embarrassing.

Well, he recently told me that he is strongly considering proposing with his mom’s engagement ring. He would get it re-set to make it more modern (read: not 70s/80s), but the diamond is basically the last shape I would want. And if we’re being honest, I’ve been pretty vocal in the past with my girlfriends about my feelings about this particular diamond cut. Of course, this was before I knew about mom’s ring. He does well at his job, and has said that money isn’t an issue when it comes to the ring, so it’s not a question of budget. For him, it’s the sentimental value.

So, my question is, how big of an asshole am I if make it clear that that’s not the ring I want? I feel it would be different if I had met his mom at any point, but I didn’t. She passed away 20+ years before I ever even met my boyfriend. This is something I will wear every day for the rest of my life, and I want to love it — I don’t want to have to learn to love it. I started to gently share my feelings at one point with him, but he shut the conversation down pretty quickly. Am I a terrible person?

– Ringless and Clueless

This is a tough one. Full disclosure: I’m typically of the school of thought that women make way too big a deal about engagement rings than they should. I understand you start mentally designing these things at an early age and your expectations are sky high, but it’s a symbolic offering from someone who plans to commit their life to you, and it sets them back THOUSANDS of dollars. That’s heavy shit. Maybe put things into perspective before complaining that your 1.2 carat princess cut isn’t 1.5, or that your band isn’t also lined with stones, or that it’s missing any of the other unreasonable features you’ve been hoping for since you were 12.

I’m going to side with you here, though. This isn’t some poor schmuck scraping up the last of his life savings just to drop to a knee with a respectable ring. This thing sounds outdated and unattractive. At least that’s how I see it in my head. And, like you said, this thing stays with you for life. I don’t know the best way to broach the subject, but you should consider letting him know how you feel again. Do it delicately, of course.

Try this. Maybe propose to him possibly repurposing the stone from his mom’s ring and turning it into an alternate piece of jewelry that you’ll wear forever and appreciate just as much. Like as part of a pendant that hangs from a necklace. Use some corny line about how it would be closer to your heart or some other cringeworthy shit like that.

Hey Dillon, how’s it going? I’m reaching out to the mailbag because dating is killing me and I need some outside advice. Background: I’m 23, a working registered nurse, have my own apartment, and pretty much have my shit together as much as a 23 year old can. I get a decent amount of attention from guys but it never lasts. I usually let the guys take the lead for the most part, but I do text first here and there and I’ll snag the check while they’re in the bathroom a few dates in. I also like to wait at least a few weeks before sleeping with them because I just don’t like to rush myself. For some reason, out of nowhere, I’m always getting ghosted. Or i’ll get a “you’re so great but this is bad timing” text a few days after an awesome date. I understand this happens a lot and to everyone, but its really starting to get to me. I’ve never been in a serious relationship or in love and I haven’t held onto a man for more than like 3 months since I graduated high school. I’ve always been more focused on work/school I guess and I do fine on my own… I genuinely enjoy my own company. I like spending time with someone I’m dating but I also do my own thing so I am absolutely certain that I am not clingy. But now that I’m graduated and everyone I know is married, or about to get married, the loneliness is starting to settle in. It would just be nice to have someone I guess. I don’t know what I’m doing wrong, but I want to fix it. Can you give me any clarity? TIA.

You’re 23 and all your friends are either married or getting married?! Fuck. Either your friends are all older than you or your friends are getting married way too early. This is the time for figuring shit out and having fun and making mistakes and traveling and being independent. Not for filing documents in court that say you’re about to live with the same person forever.

Someone much older and wiser once told me this: “Don’t have sex until you’re 18. Don’t get married until you’re 28. And don’t have kids until you’re 30.” I think that’s a solid set of benchmarks for life’s significant milestones. Okay sorry I know this isn’t what you asked me about.

I think you should try to embrace this awesome stage of your life a little more and stop fretting over getting locked down with someone.

Also, 23-year-old guys (assuming you date around your age) don’t care too much that your “shit is together.” They just don’t. They want someone they can have fun with and have drinks and sex with and who gets along with his friends. He doesn’t care that you make 55k and live in a one-bedroom and know your way around your local grocery store.

He shouldn’t want to get serious yet, and, frankly, neither should 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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