Questions From The Chase: Going Dutch, A Misplaced Texan, And An Overthinker

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Questions From The Chase

I’m sure that there are a lot of curious people out there wondering what’s going on in my personal chase for women, however, it is with a heavy heart that I have to tell you that I have laid eggs my first two weekends here in Austin. O-fer. Zip. Nada. Absolutely nothing. Or maybe there aren’t a bunch of people wondering.

In any case, this week we have three questions. Two are from a couple bros who need a little help and the other is from a girl who is not thinking very clearly. This was a nice break from the heavy stuff I’ve been getting sent to me the last couple of weeks. Please keep the questions coming, I’m open to answering anything and everything. As always, questions are in quotes below.

Hey, big fan of the chase series, best of luck in Austin. Anyways, I wanna get your take on who pays for dinner / whatever on dates? More specifically, Tinder / bumble dates.

I have no problem buying dinner and drinks for a night out but do the rules change for you depending on how you met the person? I realized a girl from Tinder was trying to use me as a free meal after the third time in a row they wanted to get dinner with no desire to do anything else. My take is the person should at least offer, I’ll pay but the gesture should be there. Thanks and keep crushing it.

First of all, let me tell you that if you are a guy and you can’t afford to treat some girl to a meal, you shouldn’t be going out on dates in the first place. I know we’re in the new age of dating, but it’s still expected that you’re going to pick up the check. It’s great when a girl offers to pay, but me personally? I just pick it up. It’s easier and the girl will usually offer to buy drinks at another spot following the meal.

Who pays for dinner and/or drinks is really just situational. I don’t usually do dinner on a first date just because the chances of the date going poorly are quite high. You don’t want to be hunched over a plate of chicken parm eating in silence because you ran out of things to talk about with some weirdo. I think you’ll find that the number of dates you go on will coincide with going dutch. By date three, I’ve found that most girls will at least offer to pay for dinner. For a first date just stick to drinks on a Friday night. You can meet up around 8, gauge the situation after one to two cocktails and decide if she’s worth hanging out with for the rest of the night.

The rules don’t change for me. There isn’t a difference between meeting some girl on Tinder or meeting one at the bar. If you’re a guy just be prepared to foot the entire bill. There isn’t really any way of knowing if someone is using you for a free meal until it happens. Sorry it took you until date three to realize that.

Dear John,

Must say this is my first “dear John” letter. Bet you weren’t expecting such top-shelf humor from an internet stranger.

I am a Texan, through and through. Just like many Texans, I love hot summers, hot winters, Texas country music and drinking outdoors. That being said, work has brought me to the barren concrete jungle of Detroit, Michigan this week. I don’t remember where you are from, but I do remember it is somewhere up north from reading your articles. Maybe you don’t know anything about it and can’t help me at all which would be sorely disappointing.

Since I will be here for about a month by my lonesome, my question is what is the key to surviving up here? Where/when/what should I be doing after 5 PM to ensure an enjoyable time? I’m staying about halfway to Ann Arbor, so I suppose that’s an option as well. 22 years young so nothing’s too out of the picture. I guess I can always find the nearest Hooter’s bar patio and drink my problems away there, but I’m looking for some insider secrets here, John. Help a brother out.

Hey man, glad you came to me for this question. I grew up about an hour and a half from Detroit and I have several relatives from there so I am very familiar with the goings on in that wonderful city.

I’m not sure if you’re staying downtown or if you’re in a suburban area just outside the city like Rochester, Birmingham, or Royal Oak. If you are staying downtown, though, the first place I’m going to suggest checking out is Slows BBQ on Michigan Ave. I’m sure as a native Texan you are a barbecue snob but I promise you that Slows will not disappoint.

As for bars? I would go to Ann Arbor for a night if you can assemble a crew. Or, you know what? If you want to fly solo do it. I don’t know why but I have faith in your abilities as a cocksman. I have a couple suggestions for where you can probably get laid. Check out Ricks American Cafe, Charleys, and Skeeps. All are a good time and you’re bound to find a nice undergraduate girl who will probably bring you back to her house near campus.

Hey Johnny,

I don’t know if you’re still doing these “ask me anything” posts, but if so, I got one for ya. I recently graduated from college and am considering going out with a guy from my school. The problem is, my college was really small, and we have a lot of….overlap. We now live in the same city and although we never really hung out in school, I always thought he was cute and just knew he was a sweet guy. The problem is that I’ve hooked up with 3 of his friends over a span of like, 6 years. Two were long term, one being a pretty serious thing, and one was just a one night stand, to be honest. He’s hooked up with two of my friends. Because it was years ago, I honestly don’t care at all, but how much do guys care about that? I’m a little surprised he’s even pursing me, because I feel like it must be weird for him. Is he just looking for a hookup? What do you think?

I guess I don’t really understand the question. Are you afraid he likes you or are you nervous he’s going to care that you hooked up with a few of his buddies? I really don’t think this will be an issue unless this guy is insanely jealous. First of all, you said that two of the three were long term things. No one in their right mind is going to judge you for that. And a one night stand? I’d be more worried if you told me you never had a one night stand. That’s a clear sign of psychotic behavior. Everyone’s had them. This sounds like a match made in heaven, to be honest. It seems like you’re keeping score and you’re up one human on him because he only fucked two of your friends. You’re thinking too much into this. I’ll never understand why girls start freaking out the second a guy shows interest in them. It makes no sense.

I’m sure he knows that you’ve hooked up with his friends if you know that he’s hooked up with some of your friends. News travels fast at small colleges like the one you said you went to. Give the guy a shot.

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