Mailbag: In-Office Dating, Claiming Domain Over Past Hookups, And Golfing Across The U.S.


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

My 30 year old coworker (I’m 24) has recently added me on Facebook, which I accepted, and followed me on Instagram. She works 2 rows down from me and things have been kinda flirty between us the whole time I’ve been here, which is just over a year now. It’s a lot of giving each other shit but always with a smile. Is there something here that she’s into me? Would this have to be a relationship or does a hookup possibility exist?


She’s into you. I’d advise against entering into a relationship with a coworker and I don’t need to get into why that’s not a great idea. A case can be made that an inner-office relationship is acceptable if she works in a different department that limits your daily interaction with her, but even then, it’s probably a no.

A hookup is in play, though. I’d recommend some upfront communication to acknowledge the risk in going there and reach an agreement that it would have to remain a casual thing. Be careful, my friend.

Hey Dillon,

Proud member of Toucher Nation here!

Here’s my issue:

My best friend from college and I had a falling out and stopped being friends about 6 months ago. Over winter break, I found out she slept with one of my guy friends who I’ve hooked up with multiple times. Let’s be clear, she knew this would upset me. I found out from one of my other guy friends, confronted her about it, to which she gave some bullshit apology claiming she was drunk and “it didn’t mean anything.” She has done this many times to other friends so I guess I should’ve seen it coming. There were other contributing factors to me ending the friendship but this was the last straw. My question is: am I being too harsh? I do miss her sometimes and we were basically sisters, like I thought this girl would be maid of honor at my wedding. I considered reaching out to her a few months ago but then found out she slept with another guy I once slept with and had a crush on and decided against it. In an ideal world, she would reach out to me with a genuine apology but I just don’t see that happening. I’d love your opinion on this since it seems like all my girl friends think this is atrocious behavior while all my guy friends think I’m being ridiculous.

I’m going to address this with a more general, broad scope.

Some people seem to think that having history with someone, no matter how brief or casual, means that person has perpetual domain over them within their circle of friends. I don’t think I agree. Yes, if you were once in a meaningful relationship with someone, it would be fucked up if your best friend started sleeping with that person after you broke up. But is there an acceptable waiting period to make even that scenario okay? I’m not sure, but I’d listen to an argument on either side.

But if you hook up with someone a couple times or got flirty with them one summer or exchanged a few late night texts, does that person become off limits to your friends until the end of time? Explain to me why you think so.

If you miss her, reach out to her. Don’t let this be the reason the friendship dies.

Yo, Dill

So basically here’s the dealio: I’m trying to get into the golf grind for business and personal reasons but I’m seriously having trouble. I’ve taken lessons from this fucking lady who says she was “on the PGA” but it looks like the only tour she’s been on was to the buffet at the course. It doesn’t help that her English is shit. So basically my question is, how long did it take you to get good at golf and did you take lessons? If so, how long? Because I haven’t broken 95 and it’s been like 3 months.

This question absolutely infuriates me. You have no motherfucking idea how difficult this game is yet. NONE.

Who said I was good at golf? It certainly wasn’t me. I’ve been playing this God forsaken game since I was eight years old and I still sometimes don’t break 90. I still suck. I still can’t go low. I still stand over the ball with limited confidence. You’ve been playing FOR THREE MONTHS. What’s the matter with you? How are you going to bring this toxic energy to my inbox like this?

Three months. Three. Months. THREE MONTHS.

Hi Dillon,

How does one have a “where is this going?” talk without making the other person feel like they’re being put on the spot?

I’m not sure what the answer to that question is but if “where is this going?” makes that person feel like they’re being put on the spot then the answer to it is most likely “nowhere.”

Hey Dilly, I’ve got some quick Q’s for the mailbag.

1) How was your weekend? Have fun in downtown on Saturday?

2) My friend is with a shitty girl, what’s the best way to make them break up (again, for the 4th time, but this time permanently) So quick story, this chick has 2 kids and 2 different dads to them. Now being single with kids shouldn’t be too much of an issue, but she was kicked out of her place and moved in with him. This was after they broke up and got back together for the 3rd time. She dumped him on a Friday, slept with her ex, then got back with him on a Sunday. This relationship is toxic for him and it needs to end, but I don’t know how to help besides telling him that this girl is more toxic than a gallon of flint water.

3) What’s your go-to office pen? Mine is almost dead and the bar I stole it from closed.

1) It was a fine Saturday. I never made it downtown, though. I did, however, have a couple drinks with a friend in my soon-to-be neighborhood (just south of DT), which is a great area.

2) Man that’s a real shitty situation. What’s tough is there’s not much anyone can do about it. The decision has to be his and his only. You can lead a horse to water but you can’t make him drink it. I think that saying applies here, right? Lead him there. Tell him how awful she is for him. But he’s got to drink that shit on his own.

3) I work on the internet. I don’t use pens anymore.

Hey Dillon,

This is a question as much for the PGP community as it is for you. Roommate and I are planning a road trip from DC to LA via the north half of the country: Chicago, Jackson, MT. Rushmore, NW (Portland), SF, and finally to my place in LA. Do you have any suggestions for courses to play near those cities? We’ll be visiting buddies in Chicago, Jackson, and SF. A course and a city to crash in for a night in between Jackson and Chicago is where we have the most flexibility.


I have pretty much nothing to offer here but obviously I’m including your question so the commenters can help you out. Have fun on your trip.


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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