Mailbag: Receiving Beneficiary Money From Your Deceased Ex, Getting Pregnant While Cheating, And Fantasy Football Punishments


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

Hey Dillon,

A few months back I was getting ready to go to the umpteenth wedding of the year, when the doorbell rang. A few detectives were at my door asking about the dentist of my ex. A little taken aback, I gave them the information I had, making no promises that it was still current. I asked why they were asking, and they informed me my ex, an otherwise healthy 32 year man had gone to sleep and never woken up. A little back story, we were together for about 5 years, I thought we would be married one day. We broke up 4 years ago and it was a fairly pleasant break up (if there can be one) and we still chatted on occasion.

After the initial shock settled, I called his mom and told her I was sorry for her loss, and I would like to come to the celebration of life if she was ok with it. Fast forward a few weeks to the celebration of life, and I walk in and EVERYONE there knows who I am. Coworkers and friends I have never met know who I am. On the board of pictures from my ex’s life, I am displayed in, or took; most of the photos from the last 9 years of this man’s life. I was mentioned in the speech, and the whole event was a very uncomfortable for me.

Fast forward a few more weeks and I receive a package in the mail from my ex’s pension company. I am still the sole beneficiary of his pension. Before Canadian taxes get a hold of this money, we’re talking $104k. I called his mom again and asked her what she wanted me to do. His mother has offered me the money, sent me a death certificate to claim it, and hasn’t spoken to me since. What do I do? Can I take this money? There’s no way in my right mind I can use this for my upcoming wedding, but can I keep this for my mortgage? Replace my dying car?


Wow. This is a wild one.

First of all, it’s very unusual for someone to make their boyfriend or girlfriend their sole beneficiary. Obviously, you two were very close and he cared about you enough to make you his beneficiary over a family member. And the fanfare you received at the celebration of life only affirms that you were a significant part of his life. Still, though, that’s very different.

So he obviously wanted you to have his pension money were anything to happen to him. It’s been four years since you were in a relationship, however, SO the question is this: Did he forget to update his beneficiary or did he leave it because there was no one, in his mind, more deserving than you?

You did the right thing. You contacted his mother. And she said you can have it. I do think it’s probably in poor taste to use it on your upcoming wedding, seeing as how the money is from your deceased ex, but, in my opinion, that’s your money. I understand there’s a pretty hefty guilt factor here, so maybe offer his mother — or his siblings, if he has them — a portion of it?

At the end of the day, though, he wanted you to have that money at a point in his life, and that never changed according to the only document that matters. Don’t spend it on lavish vacations or a mink coat. That’s flexing, and people will notice.

Hey Dillon,

Love the advice lately, as usual. This is a tough one, so bear with me.

My boyfriend and I have been together for almost two years now and are very serious. We’ve talked marriage and kids, and I’m betting he’ll propose within the next year. All is well, except for a small (read: becoming increasingly large) incident a little over a month ago (Oct. 29, to be exact).

We had a bad fight involving alcohol – go figure – and I made what was probably the worst decision of my life — to go to my male co-worker’s apartment and continue drinking/stay the night. We had sex a couple of times, none of which I remember (I had to call him today to find these details out for reasons I will explain shortly). He used a condom, according to him.

Fast forward to this morning when I take a pregnancy test because I’m late. Positive. Took two more this afternoon, hoping it was a fluke. Nope, definitely pregnant. Now, my boyfriend knows that me and this guy probably hooked up that night, but the point here is that I don’t know if I can see myself going through w/ the pregnancy if there’s any chance it’s not my boyfriend’s. I’m hoping they can clarify exactly how far along I am at the OBGYN, but I guess what I’m asking is: a) Thoughts & advice on my Jerry Springer-esk situation and b) Do you or does anyone have experience with how accurate the doctor can be with conception times?

Definitely not trying to get political at all here, but I am really hoping I’ll be able to pin-point if it was conceived in that time frame or before/after. I can’t imagine going nine months constantly questioning who the father is (seriously can’t believe my life RN).

Sorry for the length– I’m spazzing out a little and never had the Sunday Scaries like this in my life (and I didn’t even drink last night).

Any thoughts & advice are appreciated. Thanks!

Yikes. We have some heavy questions this week.

This is a shitty situation and I feel very bad for you even though you fucked up pretty badly. I have questions. First of all, I want to know how your BF knows you two “probably hooked up” that night. He hasn’t asked you?! Were you wanting to get pregnant with your boyfriend, or would this have been an accident either way? Anyway, that’s not why you’re emailing me.

Yes, you have to find out immediately if the baby is your boyfriend’s or the coworker’s. That will bring your anxiety down. Your OBGYN will be able to tell you exactly how far along you are in your pregnancy based on measurements. On visit number one, you’ll get your conception and due dates.

Here’s to hoping you didn’t have sex with your boyfriend within a few days of October 29. That could screw your plan up. If the news you receive isn’t what you’re hoping for, or if the stress generally becomes too much for you, there are many resources available for you to seek advice and counsel. Good luck to you.

P.S. Telling him you cheated is a good idea, too.

Hey Dillon,

First off, love the columns you write. Great work!

So my girlfriend of 3 years broke up with me recently out of nowhere. Didn’t see it coming at all. She said she was unhappy and needs to be alone to figure out what she wants in life. Now I was planning on marrying this girl so obviously I am devastated. That being said, all I want is for her to be happy, even if that means she’s not with me. I am basically looking for some suggestions/recommendations from you or fellow PGPers on what the best ways are to get through this because it really sucks. I have basically just been burying myself in work and trying to stay busy with my career. I understand this is going to take some time to get through but whatever suggestions you may have would be greatly appreciated!

Loyal PGPer

Time is the only tried and true antidote for getting over a breakup. The good news time is pretty much undefeated. The bad news is obviously that it takes, well, time. I know that’s not what you want to hear because we all wish there was a quick fix for this, but I don’t think there is, unfortunately.

Be patient and keep distracting your brain with your career and fun outings with friends and trips and family get-togethers and shit like that. And while I don’t fully buy into the “get over someone by getting under someone else” method of getting over a heartbreak, the company of someone else can absolutely be a nice distraction.

Dillon –

Simply put, how do you attract women when everyone else in your friend group is awkward and antisocial? To elaborate – I love going out. Even if I don’t score, it’s still a good time. But almost all of my friends aren’t on the same page – they are indoorsy, like playing video games, and aren’t the outgoing, social, try and hit on women type. They’re great people – smart, nice, but just don’t really know how to behave at bars, and as a result they act all introverted and closed-off. So a lot of women seem to judge me based on my friends when I approach them, and think I’m an introverted loser when really I’m just trying to enjoy myself and meet people. Any advice my man?

Anything helps.

You need to create a secondary group of friends, player. Keep your day 1s around to nerd tf out with, then have a second group, the cool group, who you hit the town with and hit on girls with and play golf with. Diversify your shit.

You probably have a likeminded friend or two in your second or third tier of friendships that could be promoted. Promote, recruit, and cultivate a cool group and get out there.

Hey Dillon,

I’m sure you’re familiar with the common thing in fantasy football where the person that finishes in last place receives some kind of punishment. This year in my league the last place owner has to run a beer mile. This year we had an unusual situation where the commissioner of our league quit two weeks in and moved all of his players to the bench and was basically just a bye week for any team that played him.

My question is, who should run the beer mile? Should it be the owner that quit and went 0-13? Should it be the owner that finished second to last? Or should the punishment be forgotten about all together due to unusual circumstances.

Your thoughts? Thanks.

Why did that loser quit? If this is a cash league — and I assume it is because why else would you play FF — that’s especially weird.

No one is running that beer mile, man. It’s just not happening. I’m imagining finishing second to last place in your league and you guys trying to get me to accept the last place punishment when Commissioner Dickhead went 0-13. Hahaha. No fucking way. And it’s pointless trying to get the loser ex-commissioner to run it. He won’t.

What a shitty thing to do. Taints the whole season. Fuck that kid.

P.S. My poor buddy Brad Fish has to mow the lawns of everyone else in the league in one weekend. Front yard, backyard, edge, blow. We’re spread out among Houston and Austin. Think about how terrible that is.

Sup Dorn,

Got a bachelor party in Vegas during the first weekend of March Madness. Only time I’ve been to Vegas was last December and I had a blast but it was most likely substantially less crowded then than it will be for this weekend. Wondering if you or any of the commenters might have any advice on a game plan for hitting the sports book, casinos, etc. Last time I went we chilled at Westgate for almost an entire day and it was great but I’m assuming its gonna be way too packed. Thanks in advance for helping me lose money.

PS. Always been a fan of the Roger Dorn pseudonym. The Major League movies are criminally underrated.

I’ve been to Vegas many times but never during March Madness. From everything I’ve heard, you have to plant yourself in seats and set up a home base well in advance of tipoff if you want to chill in a sportsbook during the games. But then can you even leave and come back? I doubt it. I assume your friends have to hold the fort down while you take a leak in one-man trips or whatever. Meals have to be eaten there. You’re basically camping out.

You’re not even allowed to be on your phone inside sportsbooks. It takes a lot of dedication to pull off, man. And the craps table would be calling my name the whole time. It’s just not for me.


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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