Mailbag: First Date Sex, Windshield Wipers, And No-Sex Timeouts


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

Hey Dillon! In your opinion, is sex on a first date a big deal? I’ve never been one to casually hook up and have only slept with 3 guys in my life (all were boyfriends). I usually like to wait several dates before taking the plunge. My current situation is that a guy I’ve had a not so serious but flirty friendship with for several months now has suddenly expressed real genuine interest in me. He lives about an hour or so away from me and has made it clear he wants to come drive to me, take me out and spend the weekend together. He’s already mentioned booking a hotel for himself but I’d like to offer to just have him stay over. I know he’s a generally respectful guy but I’m worried if I jump into bed with him right away, he’ll lose interest. He’s definitely my type so I don’t want to screw it up on the first day. Think it’s smarter to hold out and build up some (more) sexual tension? Thanks in advance.

I think sex on the first date is kind of a big deal, yeah. I know not everyone shares my opinion on this matter, and that’s great, but sex is a bigger deal than first date stuff to me. It’s some intimate shit and it’s not a casual thing for me. I don’t pass judgement on casual sex havers whatsoever, however.

Now, your situation doesn’t really qualify as a standard “first date” situation, in my opinion. You don’t make plans to spend a weekend with someone on a first date. You have a “not so serious but flirty friendship for several months” with this guy. While this will technically be a first date, it’s atypical of one. You know the guy pretty well and I assume you’re very familiar with him. If you invite him to sleep over, he’s going to be ready for sex. If it feels right, go for it.

Hey Dillon,

Got a bit of a doozy for you today. I’ve been in a relationship for the better portion of this year, and it’s been mostly distance. At first it was doable, but its growing to be more uncertainty of when we will see each other and for how often, and honestly it’s reaching the point where it feels pointless being in a relationship when I can’t even see the person for more than a few days every few months. On top of that, recently I find myself growing very close to a good friend in my life and I feel as thought that could be potential for something. Is there a proper protocol for breaking up with someone over distance, or am I destined to come off as the bad person in this situation?

Dump the long distance guy. What a waste of time and effort that has become for you. AND you’re already looking elsewhere? Yeah your relationship is already over; you just haven’t made it official yet.

When the relationship is long distance, a phone call is proper protocol.

Hi Dillon,

Your maturity could be useful here. Girlfriend and I had been doing fine for about 8 months until a recent issue for which I need your take came up. I was about to make that Roth IRA contribution before the S/O just about lost it on me, insisting that I should be pitching into a traditional fund! After two long weeks, still no resolution and still no intimacy since. Do I take the tax hit down the road to keep the girl happy now or cut her like a bad habit?

Either you found the most intense financially-minded girlfriend on the planet or you’re a wise guy. Imagine your significant other putting you in a two week so-sex timeout because she disagrees with how you chose the way your own investment fund is to be taxed. Great email.

Hey Dillon,

First of all, I love the podcast and think you have a really sexy voice. I have a question that makes me feel a bit crazy. I’ve been dating this guy for about 8 months and it’s easily the best relationship I’ve ever been in. We get along really great, have similar values/morals, both love each other’s families, bounce back easily from arguments, have really good sex, etc. However, we used to text throughout the day during work and lately he’s been texting me less and less. Nothing else has changed, which is why I feel like a crazy person asking this. Is it possible he’s trying to back away, or do you think maybe he’s just getting more comfortable in the relationship and doesn’t feel the need to be in constant communication? Does that even happen? I have no clue. Help me please.

Both of those are possible reasons. He may be cooling on the relationship, or he may be getting comfortable and no longer feels the need to keep the texts popping like he used to when things were new and fresh. Both can, and do, happen. I think you should stop worrying about the texts slowing down as long as all the other stuff is great. If his efforts change in other aspects of your relationship, too, then start to worry.

Have you thought of asking him about it? Communication is key.

Hi Dillon –

This is kind of a random question, but I figure you or PGP readers may have an answer for me since any guy I’ve asked just shrugs their shoulders in response. Every guy I know who drives a car without automatic windshield wipers refuses to turn them on when it rains enough to the point where they become necessary. I’m not talking about the very light, almost not noticeable drizzle. They only flick the lever manually when they feel there’s too much water on the windshield to see out. This is so odd to me. What’s the point? It seems like you’re putting in more effort than necessary when you could just turn them on to the lowest setting and not think about it. Do you do this? Do other people do this? Thanks!

I love this question. I do this. I won’t turn on my wipers until it’s become too dangerous to leave them off, then I find the lowest possible setting in order to see just well enough to avoid getting into an accident. Why do I do this? I don’t know.

It bothers me when people have the wipers set at a pace that’s faster than necessary. Seems like they’re wearing out the little wiper motor or something. And when the rain stops completely and the driver absentmindedly leaves the wipers on so that they screech against the dry windshield, FORGET IT. That drives me absolutely crazy, and I’ll usually remind them that the wipers were left on.

Guys are just weird. Maybe it’s a primal thing, like trying to deal with the elements without the assistance of technology or some shit.

Hey Dillon,

As a girl, I know I’d be irked if a female friend hooked up with someone I’ve been with– be it an ex, a casual hookup, or even a former crush. But do guys feel this way?

Recently a high school friend made a move on me despite the fact that for months, I hooked up with his best friend while they were roommates, so he was fully aware. That was a few years ago but still, it caught me off guard. I also dated a guy in college who (months before we dated) saw me make out with his roommate/ best friend.

Since this kind of thing has happened to me a few times I’m starting to think that guys just don’t care. Or are these dudes just particularly brazen?

Can you please explain this phenomenon?

– Perplexed

I think this is a bigger deal to girls than it is to guys. Maybe?

It totally depends on the level they reached in their prior relationship. Did they drunkenly make out a couple different nights at the club to “Despacito,” or did they date seriously for three years and live together? Under the former circumstance, I’d have no problem proceeding while tossing my buddy a “by the way, I asked out Lisa — that’s not gonna bother you, right?” And obviously the more time has passed, the less of an issue it is. The latter, though, that’s a no. She’s off limits as long as you intend on maintaining that friendship with your boy. Anywhere in between is a grey area and will need to be discussed with each party.

If you missed the Mailbag question about the gorilla versus polar bear hypothetical fight to the death that got its own column, read about it here.


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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