======= ======= ====== ====== ====== ===== ==== ====== ====== ===== ==== ======= ======= ====== ====== ====== ===== ==== ====== ====== ===== ====
Welcome to the PGP Mailbag, wherein I will answer questions from you, our readers. Send your questions to dillon@grandex.co. All topics welcome.
My simple question – why does almost every single person feel the need to tell you the “long time reader, first time submitter” bit before they ask for your advice? Does it give them a leg up on getting posted in any way? I’m relatively new to PGP (I graduated 4 years ago so I’m not sure why it took me so long to find you) but it seems like a good 90% of your submissions have that beginning and I want to know when did it start, why everyone writes it, and if it’s just a nice gesture everyone does to feel better before asking you something. Thank you!
It’s the classic intro used in radio format when someone calls into a talk show — “Hi, it’s Darren from Chicago. Long time listener, first time caller.” I think the only purpose it serves, if you even want to call it that, is letting the host know the caller is new and inexperienced. That’s really it. Just a fun little ice breaker.
As for the Mailbag, I think someone said “long time reader, first time submitter” once and it just caught on. And no, it doesn’t make me want to answer a question more when someone uses it.
Hey Dillon,
Been thinking about sending out an email like this since I started reading your mailbag a couple months ago, figured it was about time to give it a shot.
So my issue is that I managed to go 4 years of being in a fraternity in a major public school without having sex. To be fair to myself, I’m a decent enough looking guy (nothing that’ll make your head turn in a good or bad way) and am capable of having non-awkward conversations with women. But through a combination of a lack of closing ability, bad luck, and to be honest, some insecurity, I was never able to seal the deal.
This in it of itself isn’t what bothers me the most, I’m more worried about what to do if/when it finally happens. Should I tell this hypothetical girl beforehand and hope she understands and doesn’t bail, or should I keep it to myself and hope I can make it look like I kind of know what I’m doing? Also should being a virgin at almost 23 bother me more than it does?
Thanks man,
Hopefully not Steve Carell
This is interesting. A 23-year-old decent looking virgin who went to a large public university and was active in a fraternity, and was actively pursuing getting laid. You’re a unicorn. That is some seriously rare stuff. Impressive streak of failure. All the drunken parties and late-night hangouts with sexually active members of the opposite sex, you’d think at least a few times in all those years you’d trip and fall into some strange by accident. Yet, here you are. As pure as the driven snow.
Man, I think you be upfront about it, but in a fun, self-deprecating way if for no other reason than to take the edge off. Wait until sex is imminent, though.
If you roast yourself a little bit before the sex happens and you get her laughing with you, it’ll do two things for you: 1) It will set the bar extremely low for you, and that’s a good thing. She’s not expecting multiple, screaming orgasms that night, but you don’t need that kind of pressure anyway, because lasting just two minutes is a success for you, my dude. And 2) It makes your insecurity part of the narrative. If you’ve paid attention to the Mailbag, you know I’m a huge fan of owning your shortcomings and insecurities and turning them into advantages. This could provide you the confidence boost you need to get through this. It could end up being a really fun memory for you two.
Lastly, if it doesn’t bother you, that’s all that matters.
Hey Dillon,
Big fan of the column and podcast. great content, keep it up.
Brief backstory- I live in my hometown right now. It’s a small town, so dating is rough since I know most people my age from high school. Aside from that, I have been out of the dating game for a while for various reasons, and I have zero game left.
I work at a local gym a few nights a week as a side job. Met this guy when i first started working there. a couple months ago, we started talking more frequently when he would come in the gym. didn’t think much of it, since he is an outgoing dude and talks to everyone at the gym. I followed him on insta one day, since he popped up in my “people you may know,” and he slid into my DMs. we talked for a while through DMs, then for some reason switched to talking on FB messenger (lame, i know). now we talk pretty frequently, not every day but most days, either in person when he’s at the gym, or messaging each other. most of the time he initiates convo, but sometimes i do. we seem to click, and I’m definitely into him. (also side note- it’s been a couple months and he still hasn’t asked for my number yet (which is weird, no?)).
so, from a guy’s perspective, is he just being friendly? or is this guy into me and i should make the first move and ask him out? like i said, i’ve been out of the dating game for a minute, so i don’t wanna shoot my shot if he’s just being friendly and not into me. if i should shoot my shot, do i go for the basic move of asking him to grab drinks? in your opinion, if a girl asked you out, what would get you to say yes to a date with her?
thanks in advance for the advice.
Honestly, I think this dude has a girlfriend. I mean it’s been a couple months and the conversation hasn’t left the DMs. This feels like girlfriend territory. You need to ask him why he hasn’t asked for your number yet after all this time, because that’s a little sketch. Maybe he’ll come clean, and maybe you’ll have to follow up bluntly and ask if he’s single.
If it all works out, though, and if he is single and if he is into you, ask him to get drinks. He’ll say yes. Hundo P.
Hey there man,
I’m having a serious romantic dilemma that is just wrecking me day in and day out. There are currently two girls that I’ve been casually dating. And it’s getting to the point where it’s time to decide which one to be exclusive with. But I’ve never been so torn over a decision in my life. Both girls are funny, smart, cute, and like me a lot. Which covers the real important stuff but the devil is in the details:
Girl 1- our sex is amazing and I am so attracted to her it hurts. She is all I think about day and night. But, with our views on life (politics, marriage, family, etc) don’t really line up at all.
Girl 2- sex is very average at best and while she’s cute I could take or leave intimacy time. Sex is whatever. But, her views on life (politics, marriage, family, etc) matches with mine perfectly.
So whose it gonna be? Thanks for your help
-Fork in the Road
First of all, Girl 2 needs to be demoted ASAP. That’s harsh but real. I don’t care how cute, funny, smart, or politically and religiously aligned she is with you. This is a new relationship and the sex is already meh? “I could take or leave intimacy time,” he says. That’s sorry. Mannnnnn, you’re loco for thinking she’s potentially an exclusive girlfriend.
HOWEVER, you don’t need to be exclusive with either one of these chicks right now if things like politics, marriage and family are important to you, and it seems like they are. Girl 1 sounds pretty dope, I have to admit, but why sign her to a longterm contract if you know she doesn’t have franchise player type stuff? Date Girl 1. Have fun with Girl 1. Take Girl 1 to do awesome shit and get her naked often. But keep it casual with Girl 1.
Don’t go exclusive until it feels right.
P.S. I hope the two girls know about each other since sex is happening with both. That’s my policy but it should be everyone’s policy, if you ask me.
Big Dill,
New reader but big fan of the mailbag, literally have been binge reading it for the past few weeks.
So I am 22 years old fresh out of college and just got a pretty decent paying job (decent enough that I can afford guac at chipotle now) pretty close to DC. So being excited about my new job I posted a picture of my business card online and this girl commented saying she lives real close to where I work. Said girl has been a crush of mine through like junior year of college, however I have never shot my shot with her and have only once been to the bars for her birthday with a bunch of other friends. So I slide in her DM’s and say we should hang out some time. She messages back and agrees to happy hour the next day (today).
My question is what is the best way to let this girl know that I am very interested in her and not just trying to be friendly / how do I let her know that I want this “hang out” to be a date? College for me was literally just drunken hookups and one relationship that ended very badly after like 8 months so I know nothing about adult dating aside from the fact that I’m supposed to cover the bill.
Also do you or the readers have any tips on working with all women? There is not a single male that works in my office. And these women are all like middle aged.
Thanks boss
You’re (assumedly) heterosexual members of the opposite sex around the same age getting drinks together. You don’t need to let her know this is a “date” because what the hell else could it be? Has a guy ever in the history of western civilization asked a girl (or a girl asked a guy – vice versa) to get drinks with the intention of making a new friend?
She knows it’s a date, man.
Dillon,
Big fan of PGP, been reading articles for several months now. Now down to business. In approximately 7 days I will be arriving in Austin for a wedding. I took all of Friday off, and got a 9 A.M. flight out of Denver so I could enjoy as much of my day off as I could, and I will be arriving in Austin around lunch time. That being said, most of my buddies don’t get into town until later Friday or Saturday morning, so I’m gonna have some solo time to kill. Basically I’m wondering what suggestions you have for breweries/bars/food/happy hours etc. that someone who has never been to Austin should check out. Thanks in advance for the help.
Cheers
Your Friday night and Saturday morning/afternoon plans can be found in today’s episode of Touching Base:
Show up looking fresh as hell..
The more questions I receive, the better this series is going to be, so send me your Mailbag questions to dillon@grandex.co and please put “Mailbag” in the subject line.
Respond
Dillon Cheverere
Dillon Cheverere is the Vice President of Media for Grandex, Inc. Email: dillon@grandex.co
@dcheverere
@dcheverere
RogerJDorn
Fella with the unchristened pecker, if it makes you feel better I’ve had sex loads of times and still rarely last 2 minutes. Just go down on her first, it gives the impression that you tried.
Buddy why are you giving away our trade secrets all willy-nilly like this??
Steve Carell: just put that in your Bumble profile. It’ll be funny.
Gym girl: guy has a girlfriend for sure. Tough luck.
Fork in the Road: threesome, you dummy.
Cannot believe there have been ZERO “sup” comments for our virgin friend so far. Get it together, ladies.
If I was single I would’ve thrown the sup
Girl meeting the dude at the gym…I’d bet the house he has a girlfriend. Run away.
As far as the choosing between two girls question…I didn’t know Arie was a fan of the site…
First thought this was Arie satire, but neither of the girl descriptions was ‘totally lacking in all interesting qualities but looks great on my arm’.
You know that dude was just having Lauren sex flashbacks after they got engaged and he finally just snapped. Lauren is nothing more than a sexy brick wall
I’m probably gonna get downvoted like crazy, but to the virgin 23 year old… few years older than you and in the same boat — was worried like hell about it but realized throughout the years, and talking with some close friends, that it’s nothing to really be ashamed of. Just be you, be happy with who you are, and you’ll find that people will actually respect you for it. Just my experience, but hang in there man
To the 22 year old who asked the girl to drinks-
This doesn’t happen often, but I disagree with Dil. Make sure you’re clear with this girl that you’re interested and want this to be a date. I took my shot earlier this year because that’s what we do in 2018 and later had to clarify to a girl that my intentions were for a date. I used the words “Let’s go out together” so you can’t say I wasn’t clear. Long story short, I no longer had a date that week.
Agree with this, I would likely accept drinks with an old friend/ acquaintance to catch up without necessarily being interested in dating them.
I disagree with Dillon as well. I live in Washington DC and when an acquaintance from college moved here and asked me to drinks, I thought nothing of it other than he was new to the area and trying to make friends. I realized he thought it was a date when he tried to kiss me goodnight. We became good friends (friends are hard to make in a new city postgrad) and can laugh about it now, but do not assume its a date.
Yeah just text her and literally ask if it’s a date, if she says no you just saved money and time. (Go if you’re still into being friendly) but if she thinks it’s a date and she says yes then it’s way easier, no trying to figure out if it’s a damn date or not while you’re on the date.
I recently dated a virgin and while I was weirded out at first, I quickly realized it was great because I could mold him into exactly what I wanted in bed. Be honest and up front about it, but let her know you’re ready to learn, then she’ll be more excited about it.
“mold him into exactly what I wanted in bed” JFC, we’ve got a female Christian (Christina?) Grey over here…
that being said…sup?
Spot on. Plus it eliminates the whole “wonder what girl he learned this with…” thought.
To the 23year old 40 year old virgin. Bro no sweat it happens to the best of.. you. Not sure what your story was, be it you had chances to get laid but you had some serious performance anxiety where you got in bed with a girl and just can’t get the deed done because you were nervous or you just never got that far to begin with.. but a girlfriend definitely helps with either of those. Don’t get one solely to give her your V card though, just someone that you actually like and can get really comfortable with that will make being naked around not nerve wracking. Chances are she’s not a virgin and can help walk you through the basics. Godspeed fella.
To the 23 year old with the pristine peen: dude, you’re missing out on literally the only free form of fun left for humans. That being said, it’s really not a big deal at all especially when you take a step back and realize that rubbing 2 things made of skin together for ~90 seconds to make stuff come out is as good as it gets for our species and that’s pretty fucking sad lol
Free? You always pay for it one way or another. Marriage, dinner, prostitution. It’s all the same really.
Dammit, you’re right. The cats out of the bag, we’re gonna have to blow this shit up now
I spit out my soup reading this comment. Bravo.
23 year old virgin- I’m a girl, so slightly different scenario, but I lost mine at 23. Wasn’t saving it, just never ended up happening for various reasons, but long story short it wasn’t a huge deal. I went on a couple of dates with a dude and when we started to hook up I told him the deal and he was very cool about it. We slept together on date 3 and it wasn’t weird since we had talked first. We didn’t go out very many more times but no regrets, he made something that could have been awkward comfortable and fun. I wouldn’t keep it a secret but would advise only mentioning it if you think it’s about to be relevant. Definitely don’t try to keep it a secret, that will make you both uncomfortable for various reasons. Some people like feeling like they can teach you something, too. Good luck!
To the virgin- I dated a virgin for about two months my sophomore year. She was comfortable with everything else so it worked out. So just stay the course with the “bases”. However, she eventually did anal so I realized she was just *that* catholic girl