Mailbag: Getting Into The Dating App Game, A Significant Other Who Is Spiraling, And 5-Year High School Reunions


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

Hey Will,

First off I always enjoy reading your critiques of insufferable millenial culture. That being said I need some help. I just got out of a relationship that started before I had a smart phone. Yeah. Crazy right? Anyway I feel like I’m totally lost when it comes to being single in 2017. I’m trying to figure out dating apps but it’s just so overwhelming. There’s way more than I thought and once I get a match on one I’m so confused about what to do. Any chance you could give us newly single people a for dummies summary of what’s out there?

Note: In the spirit of transparency, I have to tell you that this question was obviously sent to Will and he passed it on to me since he’s out the game.

Your smart phone comment leads me to believe you’re north of 28 years old, maybe even well north of 28. Unless you’re into some weird shit that would necessitate you connecting with a very niche demographic of other weirdos, you really should only think about using two dating apps: Bumble and Hinge.

Tinder is a very popular one but it skews younger and is generally thought of as the “hookup” app.

Bumble is unique in that the girl has 24 hours to initiate the chat — conversations usually start with a simple “Hi,” “What’s up?” or “How’s your week going?” comment. Then it’s off and running. Hinge provides more in-depth profile options which makes me associate it with people who are looking for more serious relationships.


First and foremost, I love this column. Keep it up, some of the e-mails I have been reading here makes my day after work. In order to explain my situation, you have to understand a bit of who I am.

I’m a 25 year old male living in Richmond, VA. My life is going very well in most aspects. I have my shit together with work, health, financial stuff as well as relationships with my friends and family. A lot of great things are happening for me, except for just 1 thing, which honestly, makes me very scared.

I graduated from college about a year ago and I was in a fraternity. My time with the fraternity changed who I am and made me see the college lifestyle in a very different light. I was a goody-two-shoe’d kid growing up, so the change was big for me. It was so big that I got carried away my years there and had sex with a lot of women and never truly dated, mainly because I saw college as a time where I shouldn’t take life so seriously and just enjoy myself. I’m not going to lay any specifics, but I always bought the 30 pack of Trojans at Wal-Mart every 3 to 4 weeks. It was nuts, and it came to full circle after graduation, where I had to be a lot more responsible in the real world.

So ever since I graduated, I ditched my man-whore ways. I have never loved anyone outside my family, keep in mind. I was an avid tinder/bumble user, and now I am finding all the wrong types of women who claim they do not have their shit together in the city. Dates would go great as usual, then the normal response after the 2nd or 3rd date I get is, “You are a great guy, but I am just not ready to see anyone, I hope you understand and we can be friends at least” and “Any girl would be so lucky to have you.” And that just simply does not work with me, I move on because I know I deserve someone who does have their shit together. I have been on many dates with almost just as many women with no results. Honestly, I fear I’m going to be the only guy in my group of friends who is single because “he isn’t dating material.”

So I’m writing for advice. What should I do to get over this obstacle? I was thinking deleting tinder/bumble altogether and just hope one day it happens and clicks, even though that is not in my nature at all. I was also thinking of switching to Match/OkCupid for better compatibility, however I am trying to get away and put aside the app/online dating scene. Any advice from you or from the commentators would be greatly appreciated, thanks Dillon.

A changing man

First of all, congrats on the sex.

If you’re trying to meet someone and enter into a meaningful relationship, I’d shut down the Tinder account. I could be wrong on this (I don’t use Tinder), but as I stated before, I just don’t think that’s the place you go to find that sort of relationship, especially since you seem to be a younger guy and thus set your age range to younger girls.

Secondly, in my experience, most of the time when someone, guy or girl, says anything along the lines of “You are great, but I am just not ready to see anyone,” it means they’re not into you. If they truly liked you, they’d want to keep seeing you. It’s that simple. Of course there are exceptions, but “Any girl would be so lucky to have you” actually means “And it’s never going to be me.”

Just keep going on dates, man. It doesn’t matter how you meet them, but keep meeting people and taking them out. You’ll find a match eventually. And I’d think of apps as simply a means of initiating contact. Use them but don’t depend on them to fully vet possible significant others. That happens in person.

Hi Dillon,

Big fan of the mailbag and your advice. This one is dramatic, so prepare yourself. I’m embarrassed to even admit that I’m in this situation. Basically, I live with my boyfriend and we’ve been together for a year and a half. He’s 46, I’m 29. We have an amazing connection and when he’s sober, our relationship is great. I’ve always thought he was the one. We’ve talked marriage and are very committed to each other. That said, the past few months have been a rollercoaster.

Essentially, he was laid off from his job about three months back as a VP. He has been looking for jobs but hasn’t found anything he wants yet. So, he’s been sitting at home job searching/watching TV/doing nothing. Like, he has got to be depressed. When I was unemployed for a month earlier this year, I spent it at coffee shops job searching, working out, laying out by the pool and just all around trying to have a life. He does nothing of that sort.

Fast forward to the current situation: He has been blackout drunk for the past 12 days. Not just at night, around the clock. He’s so obliterated that he can’t even string together a sentence, and his right eye has some sort of alarming red infection/bulge and he doesn’t know how it happened. As you can imagine, my home life has been absolute hell. Every day, I come home from work to find him either passed out or drinking and angry. I stayed with a friend this past weekend and we came over to get the dog, and he had filled the dog’s water bowl with beer. It’s really that bad. He’s stayed at a hotel the past two nights (I think out of shame) and all my friends are confused as to why I’m still with him. I’m contemplating ending things but I also know he needs serious help — but isn’t willing to get it.

The other issue here is our lease. We’re both on it, and it’s not cheap to break it — and I definitely cannot afford to. What’s your advice here? I don’t want this life but I’m (embarrassingly) scared to leave him.

Holy shit this dude is SPIRALING.

Look, this guy needs serious help, and it will only get worse from here if he doesn’t get any. I imagine losing a high-paying job that far into your career could take a serious emotional toll on a person. He’s in a dark place. You obviously care a lot about this dude, so do everything you can for him. If you can’t convince him yourself to get professional help, get his friends and family involved. Make sure you articulate how serious the problem is and ask them to help you out in getting him in to see a counselor at minimum.

He’s not a lost cause so don’t treat him like one. This is still fairly new. He just needs to lean on his people around him, and that’s mainly you. Good luck and Godspeed.

Dear Dorn,

Just wanted to say I have enjoyed the transition from TFM to PGP. I have a issue that has escalated. Backstory is a year and a half ago one of my best friends started to date this girl. There was conflict in the beginning as she was being wishy washy like talk to other dudes and disappearing, but he kept pursuing and they eventually started dating.

Well after a while the core friends were starting to notice some of the bad behavior still with this girl, but my friend kept ignoring it. A note about him, he had trouble meeting girls in the past and would get really sad about potential being alone the rest of his life. Well she started to notice that we were noticing, but my friend was still ignoring the signs.

Well about 6 months ago, one of our friends called her out on her BS and because he was a wild card (See Drunk) she made him believe he was a bad friend for starting false rumors. So the friends group has split. Fast forward to now, he proposed to her and asked me to be the best man. Every time someone told him some flaky stuff she would do, he would tell her and they would collectively block them out of their lives. I want to tell him to dump this succubus, but it has gone too far and I’d hope he would come to his senses by now.

Should I get him away and tell him or should I follow bro code and let nature take its course? Any advice would be appreciated.

Thank you,

Best Man in Distress

This one is tough to call because you provide zero specifics. Your descriptors are “wishy washy” and “flaky” and general “bad behavior,” but you don’t mention a single thing she has done to earn these labels. You said she talked to other dudes but you also said it was before she was even dating your friend, so there’s no technical wrongdoing there.

I’m not saying you’re wrong here, by the way — she could be the devil — but I’m not fully committing to your team until I know some deets is all. I hope you have all your ducks in a row before bringing this up to your boy, which you should do if you fully believe in what you’re relaying to him. Be careful, though. It’s a long limb you’re walking out on.

The move is to tell him your concerns then back away to leave him with his thoughts.


Some jabronies from my high school are trying to organize an official class reunion after just 5 years. We went to a smaller school, so if this thing picks up, most of the class would be expected to show up.

High school happens to be where I peaked (pgp?), so I might be able to toss some weight toward pushing things back to a more normal 10 or 15 year mark.

How do I frame this as a poor decision without outright calling them fools?

I’m inclined to think your high school friends (and you, sorry) are a bunch of dorks. Under no circumstances do you guys go rogue and plan an impromptu five-year reunion just to hold onto that brief period in your life when you were a part of actual social circles. It’s a BAD look.

The saving grace for you here, though, is that at least you can admit this is a poor decision. Go with your instinct here. Dork.


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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