Manic Monday Mailbag

Manic Monday Mailbag

Mondays can be tough. That’s why every Monday from now until you die, I’ll be doing the Manic Monday Mailbag to keep us both entertained. You can submit your questions by clicking “Mailbag” on our submission form, tweeting me at @WRBolen, or emailing Be sure to include your first name, city, and any other information you’d like included.

Q: I met this girl a few months ago, and we really hit it off. As it turns out, the company her dad is the president of was my first job interview out of college. When he found out that I never got a call back letting me know either way, he raised hell in the HR department. Long story short, I was offered a job an accepted it. I hide the fact that I am dating the boss’s daughter from everyone at work, mainly because I don’t want to give off the impression that I’m favored. Do you think this the the right approach? I’m sure people will eventually find out, because her dad stops by and talks to me a couple times a week. I just don’t want people to think I’m getting this shit handed to me on a silver platter. Please advise.
—Adam in St. Louis, MO

No Adumb, that is not the right approach. Your situation is one that millions of men would literally murder an innocent stranger to be in. As long as you don’t blow it with the daughter, you have an unlimited “Get Out Of Jail Free” card. You should be strutting around that office like you own the place, because in a matter of years, you probably will. Walk into the HR department, take one big handful of your own balls a la Chris Brown, and just stand there for an hour or two, staring daggers at everyone. Embrace the silver platter, for it is the finest dish in all the land.

Q: Have you ever sat on a hard chair aquwardly for a while and it cause your dick and grundle area to go numb? It’s a weird feeling like a numb foot but in your swimsuit area. Is this just me? Has it happened to you? How do you solve this? I need answers.

First, I can’t believe that’s how you think “awkwardly” is spelled. Second, I can’t believe you refer to your package as your “swimsuit area.” Everything about this question points to you being a terrible sexter. Yeah, I’ve sat awkwardly before and had my ass, thighs, or grundle go numb. Just stop sitting that way, you silly doofus.

Q: As the seasons turn, I find myself masturbating solely to double penetration porn, sometimes even triple penetration. While I swear I only consciously look at the girl as she is being stuffed beyond comprehension, part of me wonders if I subconsciously just want two or three penises visible every time I furiously yank on mine. The “I’m kinda looking at a naked guy’s dick here” feeling has always been present in porn unless you’re only watching girls go at each other, but when there are two or three times as many guys in the frame as there are girls it really makes me start to wonder. Do you think I am bisexual or do I just have a strong taste for stuffing like a true American during Autumn?

Some guys can watch porn with seven, even eight dicks involved, and as long as the female actress is of a worthy caliber, they’re undeterred. It takes Jedi focus, but you have to see past all that man meat and focus on the task at hand. Odds are you’re just into really weird shit. That being said, you’re on your way down a slippery slope of sexual perversion. Before you know it, you’ll need two Mexican day laborers choking you and a bulldog licking peanut butter from between your toes while you watch quadruple penetration on a 3D TV just to get off.

Q: I recently acquired a Blackberry for work and have taken on the status of a two smartphone man. I’ve been carrying both around in my pockets (one left, one right) and this has become uncomfortable, not to mention I’ve doubled the amount of radiation headed for my sack everyday. I’m out of the office all day, so leaving one on my desk is not an option. I’ve consulted a few people on whether or not it is socially acceptable to get a belt clip and I’ve gotten varied responses ranging from power move to absolutely not. So Bolen, I need some help.
—Grant in St. Louis, MO

The belt clip is like the Bluetooth ear piece; it makes you look like a huge tool. If you’re an engineer, or in some hardcore field of work where you do man shit all day, then maybe you can pull it off. Otherwise it’s out of the question. Keep carrying them in your pockets and take the risk of possible testicular cancer. That’s a power move.

Q: I’m talking to a girl that is a solid 8, and pretty cool, but there’s a problem: she’s not about hooking up at all. We have before, and it’s not like we haven’t been talking long enough or anything like that, because this girl is all about me. Apparently this has been a problem in essentially every one of her relationships, which she blames on “guys only wanting to be with me so they can hookup with me.” Is it just me or is being physical pretty important in a relationship? It would be different if we had never hooked up, but that boat sailed about a month and a half ago. I need some advice on where to go from here, my man. It feels like I’m about to date a damn monk for Christ’s sake.

Ouch. That is a shitty situation. Sounds like this chick has some serious trust and intimacy issues. The solution really depends on how much you care about her. If this is someone you can see yourself with long term, and your feelings for her are strong enough that you want to be the one that helps her work through these issues, then stick around and give it your best shot. Otherwise you might need to let this one go.

Q: So I’ve been trying to get my girlfriend of about a year to let me out it in her ass, but she won’t fucking let me. I’ve offered lube, foreplay, whatever…no luck. Should I just accept that it isn’t going to happen or get really creative and come up with a way to let me get it in? She’s scared it’s going to hurt because she can’t even put half my piece in her mouth (kind of proud of that). Can you help me out here? Thanks.

Get a smaller penis.

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Ross Bolen

Ross Bolen is a New York Times Bestselling author, co-host of the Oysters, Clams & Cockles: Game of Thrones podcast, co-host of the Back Door Cover sports podcast, 2017 Masters attendee, bigger and more loyal Rockets, Astros and Texans fan than you, cheese enchilada aficionado, and nap god.

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