Mailbag: Paying With A Gift Card On A Date, Telling A Guy You Only Want Sex, And Which Dates You Make Your Moves

Dillon Mailbag

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

Note: I woke up at 3:20 this morning and didn’t go back to sleep because my brain is broken or something, so I hope my answers make sense.

Dillon the Most,

First time, long time, big fan, etc. I have a question that I’ve been stewing over for a while. When is it appropriate to use a restaurant gift card on a date? I personally think using a gift card anytime before the 5th date makes you look cheap, so I’m always refraining until then at the earliest. I’ve got a gift card for a delicious local Mexican spot burning a hole in my pocket so I thought I’d get your opinion on the matter as well as those of the PGP community.

Stay Trill

Unless you have a dynamic enough personality to make the gift card part of the narrative, I’d say around the fifth date sounds about right here.

Listen, though, you can pull it off date one or two if you’re a funny, savvy dude. Make it part of the narrative. Let her know going in that you’re pulling out a gift card when the check comes because you’re the bad boy of dating and people said you couldn’t do it. Something like that. It could be an ongoing topic of conversation, too. “You don’t think I’m gonna do it, do you?” That shit’s funny to me.

P.S. “Dillon the Most” is fanfuckingtastic.

Hey Dillon,

I have two questions, but they both sorta have the same theme so I’ll throw them both out there. Basically, how do I tell these two guys that I’m very much interested in sleeping with them without looking tacky or desperate?

Here’s a little backstory: I recently quit my job and will be relocating to my favorite city ever (very excited!), but before I settle in I’ll be doing some traveling. Now here are the two scenarios I’d like your help with:

An old friend from college is in the city I’m going to visit and we have hooked up once before. We’ve already discussed meeting up and have chatted here and there since college, but nothing explicitly sexual, though he has said he’s “very single”. How do I bring up hooking up? I’m not opposed to straight up saying “hey, let’s fuck”, but I don’t think that’s the classiest option.

This next scenario is a bit trickier in my opinion. So in the job I just quit (executive assistant), I worked with our Board of Directors. One of the guys on the Board is super attractive, single, AND happens to spend about half of his time in the city I’m about to move to. I feel like he’s been really flirtatious with me and has made comments about me looking good so I would guess there’s some level of interest from him. How do I hit him up about getting together? I think I’m mostly just nervous about the fact that he’s quite a bit older and I was in a much lower position when I met him, ya know?

Any help is appreciated—I need to get laid stat.

I’m approaching this from the perspective of which type of text I, as a guy, would want to receive if I was down for some casual sex. “Hey, let’s fuck” is too aggressive for me. It gives off the vibe that I was one of many people in your contacts getting the same exact text.

Maybe I’m wrong but it seems like you’re not interested in going/hanging out with these guys, and you’re merely wanting to get down to business. Great, but that’s a tricky proposal to deliver. I would want full disclosure, I think. I’m talking an explanation of what it is you’re looking for. A text that begins with “Look, I’m going to shoot you straight…” and ends with you telling me you want to hang out at one of our homes, or even as bluntly as “I’d like to have sex with you” would work.

You gonna get laid.

Dear Dillon,

I’ve been a fan of the column for a while and honestly have a problem with this one female at my school.

There’s this one girl that is actually a year younger than me and actually lives the town over from me. I was introduced to her through a friend that I worked with and we began talking here and there at school. When we go out to the bars, she would text me asking me where I’m at and vice versa. I’ve tried making moves but she seems hella awkward at the bar, and end up just going for someone else. She snapchats me every once in a while and makes it seem like she’s into it.

I finally said fuck it and said we should do something now that we’re home and get food or some shit and she agreed, but now she hits me with the “I’ll let you know” when I ask when she’s free? Do I shoot my shot now that it’s 2018 and let her know straight up that I’m into her and we should do something, or just let it go and move onto bigger and (hopefully) better women?

Any advice is greatly appreciated

2018. Is. The. Year. Of. Shooting. Your. Shot.

Dear Dillon,

First off, huge fan. Love the content and podcasts.

This email turned out way longer than I planned so I guess read if you’re interested in our back story but in essence I am asking two questions:

1. How much of a shitshow is Austin City Limits in the frame of keeping the unity of a bachelor party?

2. What can we expect from Austin as a whole that weekend. It’s the second weekend of Austin City Limits AND UT vs Oklahoma.

About 6 months ago my best friend gave me the honor (and stress) of being his best man. Obviously I want to throw him the best (i.e. stress free) party I can, as our last experience with a bachelor party in New Orleans gave us permanent anxiety. One of our biggest problems is the best man at the time did zero research and we spent 4, I repeat 4, as in one more than 3 days, on Bourbon St.

This time however I have the reins, so shits gonna get diversified. In Austin.

First off, mid day flight on Friday, mid day flight Sunday. Airb&b on west 6th. And all the bars I could research from PGP podcasts. I have been twice as an undergrad and only remember arriving and leaving broke but very satisfied. I think there was a river in there at some point.

To organize the trip I took a whole democratic approach and let the group vote on the destination, excluding the groom. After we finally landed on Austin and figured the dates, which are unflexable due to international groomsmen coming in, I learned in horror, that it was UT vs Oklahoma weekend. I have had personal experience with this weekend in Austin wandering around 6th st wondering if I dreamt it was a party town instead of a ghost town. Fast forward to today where I just learned ACL will be that very weekend. I am conflicted. I love the idea that the town will be alive, but I am worried about how this turn of events could negatively impact the unity of the bachelor party experience. Do you have any experience with this? How does Austin handle with college kids in Dallas and flood of tourists for ACL in Austin?

Any and all advice is welcome.

Austin City Limits is just like any huge music festival. It’s a big, open field (Zilker Park) filled with tens of thousands of people. You can keep the unit together pretty easily. A lot of squads bring flags that they use to let their squad members know where they are in a mass of people. It works.

ACL is obviously a huge deal those two weekends, but Austin is a big city filled with lots of people who like to go out. The bar districts carry on as usual, but crowds will be a bit smaller. Ghost town? Nah. And the Texas-OU game doesn’t affect the Austin scene too much except that the bars will be showing the game. Plus the game is always either an 11:00 or 2:30 kickoff so it’s out of the way before a night out.

In episode 125 of Touching Base, we tell you all you need to know about planning an Austin bachelor party. Listen to it.

P.S. Two-night rule for New Orleans and Vegas. Two nights only. No more, no less.

Hey Dillon,

So I’ve gone on a couple of dates with this girl I really like and they’ve both gone well. It’s definitely early, but I’m wondering when would be the time to move for a kiss or to make it official.

I’ve been in these situations before, but every first (kiss, relationship, sex, etc.) was initiated by the girl those times (I’m not an irresistible sex god, just lucky). When do you think would be a good time to make the first move on either front?

Kiss her now. Do it now. Right now. First kiss is either date one (if it’s going well enough) or date two. It probably happens more on date two. If date three ends without a kiss, you don’t deserve a fourth date.

You’re asking when it’s time to make the relationship official? Let’s slow down, sir. You don’t need to be thinking about that quite yet. Besides, there is no rule here. It’s a circumstance by circumstance basis.

Sex first happens on dates three, four, or five. Yeah that sounds about right. Feel free to initiate if and when you think it’s what she wants, too. Make moves.


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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