Mailbag: Living With Your Significant Other Before Marriage, Settling For Bad Sex, And Turning Grey At A Young Age


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

Hey Dillon,

I’m 27, and all of my best friends and myself seem to find ourselves in serious relationships for the first time in our life. This has led to some discussion over the time-line such relationships take, meaning, when did you say “I love you,” have you met his parents yet, have you talked about marriage at all, etc… Through these talks I also realized that there is a built-in presumption that everyone will live with their boyfriend before getting engaged or married.

Recently, I am realizing that I am the only one of my friends that has a hard no on living with someone before marriage. Now, to be clear, I am not saving myself in any way… that ship sailed a decade ago. I’ve held this position for a number of other reasons, first and foremost out of fear that my ultra-conservative Catholic family will disown me and not pay for my future wedding should that proceed. But even more so, I just want to leave something exciting and romantic for after marriage, as well as keep my independence as long as I can. Also, if I’m going to move all my life into a cohabitation situation with someone else, I expect them to have to hire a lawyer to get out instead of just a 30-days notice for me to find a new home.

As for my own relationship, I’ve already voiced this stance to my boyfriend who seemed to take well, albeit he had always assumed he would live with someone when he was serious enough. But after realizing I know absolutely no one my age who seems to hold this same view, I’m beginning to wonder if I am the only person who doesn’t want to live with someone before marriage? Really I’m wondering if you could offer some insight into your thoughts on the subject as maybe I’m being unreasonably stubborn/judgmental of other relationships in being so adamantly against it. Any thoughts would be much appreciated!

I don’t think you’re “unreasonably stubborn or judgmental” of others who choose to do this, because it seems like you actually accept that your friends want to do it, BUT your way of thinking is very old school, traditional, and outdated. There are very few of you out there in 2017.

The religion thing I understand is big for some people. Respect. I won’t touch on that. But you start to lose me here:

“I just want to leave something exciting and romantic for after marriage.”

Why? What’s more exciting about living with someone you’re married to as opposed to living with your boyfriend? It’s the same thing, just with papers. You’re in the same bed, cooking in the same kitchen, laying on the same couch, and having the same sex. Here’s a little secret of the pros: Shit is the same after you’re married. Nothing really changes except your last name and the way you file taxes. There’s no “special” feeling you have after the newlywed phase wears off, which is brief, by the way.

I encourage you to reconsider your stance on this. You don’t know your boyfriend as well as you will once you live with him. You two could be totally incompatible when you sleep under the same roof each night. It’s the buying a car without test driving it first theory. Don’t forget thatmarriage is supposed to be a lifelong commitment. LIFELONG. Do it right.

Dear Dillon,

First off, big fan of PGP’s Touching Base. Your suave persona really seals the deal. If you ever wanna kick it in Ireland and golf sometime with me and my family, hit me up.

Let me premise this with a little background. I dated the same guy for all of college (I know, big mistake, right?) completely thought we were gonna get married, the whole nine yards. My ex didn’t pay for ANYTHING. I literally paid for his meals, gas, clothes, etc. I was basically an ATM. Never got a present from him for my birthday or anything. You can delete this if you see fit.

Broke up right before my graduation, before I was tossed into the sea of post grad life and post grad dudes. Forward to today. “Dating” this guy who spoils me. I had $90 ramen the other day. Spoils. The. Frick. Out. Of. Me. The thing is, he’s younger than me. Is it weird that that makes me uncomfortable? The other thing is, we have no spark. Literally no chemistry. Is there a way I can change this?

With high respect,
The Lost Girl

I really want to know what $90 Ramen is all about. Is this a real thing? It’s like 11 cents at HEB.

Yes it’s a little weird that him being younger makes you uncomfortable. Just a little weird, though. His parents conceived him after yours did you. Who cares? Unless he’s a generation younger or some shit, but I don’t get the feeling that’s the case here.

“The other thing is, we have no spark. Literally no chemistry.”

No offense but why in the absolute FUCK are you dating someone you have zero spark with? I don’t get it, and frankly I find it a little upsetting. You’re basically telling me “I know I can be much more fulfilled with someone else but I’ll settle for this guy.” You have one life to live. Go find your damn spark. Go have awesome sex with a dude you can’t keep your hands off of. That’s chemistry. That’s a foundation to build on. Tell him and his $90 Ramen it’s been fun and the Ramen was bomb but you have to find someone else.

P.S. Yeah let’s play golf in Ireland with your family. I’m not buying you expensive ass Ramen, though.


Hey man, headed to Austin for a business trip. Two days and I’m working mostly so time is pressed. What’s the one thing you “have” to do in Austin? Also, I think you should do a new video series where people challenge you in throwing a football. Ross can bet it, feel like he’d be down.


The Austin nightlife is the one “must.” Rainey or West 6th are the places.

We’ve talked about this a bunch recently. I may put a plan into motion for a video series. And yeah, Ross will bet on literally anything. I’d be favored in each throw-off. Believe that. I could only do one every couple weeks at most. I’m older now so the arm takes a little longer to recover these days.

Hi Dillon,

Love reading the mailbags and your responses.

So my girlfriend’s sister is getting married in about three months and I’ve been given the official invite. This is the first wedding I have ever been invited to. To my knowledge it is an open bar. What is the protocol in terms of tipping the servers/bartenders? Should I drink next to nothing in order to make a good impression with extended family? My girlfriend wants to have fun (wink wink) but I also want to stay in the good graces of her family, many of which I am meeting for the first time. Any advice for a first-time wedding goer? Thanks

Does “have fun (wink wink)” mean she wants to do drugs? Serious question. If so, don’t do that.

Tipping is rare at open bar weddings. They don’t expect it and usually won’t have a tip jar set out. Their gratuity is typically covered by the bride’s family. You can tip in a “pour it heavy (wink wink)” type of situation, though. That’s very appropriate.

As much as I hate to say it, you shouldn’t get annihilated at this wedding. Not with her family there for an occasion like this. Drink enough to be extra social, but you don’t want to be the guy grinding his dick off and sucking face on the dance floor with his neck tie turned into a makeshift headband. Not a good look.

Mr. Chevererererererererere,

I recently noticed on Instagram that you were sporting some salt and pepper ‘burns. Wanted to see what your opinion of salt and pepper ‘burns are and what age you think it’s appropriate to just let them be. I personally can’t wait for the day I get to roll with the touch of grey.

I’m proud of my gray hairs. Most girls seem to be into it while guys tend to give me shit for it. I’ll take that. My dad has turned basically solid white up top. That might be in my future, and I’m okay with it.

You are implying that young guys should maybe dye their hair as grays start to creep in. No. Don’t do that. Let that shit go. It’s distinguished as shit and most girls like it.


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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