Questions From The Chase: Rosters, Condoms, And Everything In Between

Questions From The Chase: Rosters, Condoms, And Everything In Between

I’m calling one of the better “Questions From The Chase” segments because 1. I had more than one anonymous question come to me this weekend and 2. because I’m going to give you some hard truths that you might not like. So let’s get into it. Submissions are in quotes, and as always, keep em’ comin’. Our first question today comes from a girl who is in a bit of pickle.

Johnny Johnny Johnny. I’ve recently started hooking up with this guy but we haven’t slept together yet… I know. First time: I didn’t want a one night stand. Second: out of commission for girl reasons. Third: whiskey dick. Honestly I am a little uneasy about fucking him because I don’t think I’m the only girl in his rotation and that both bothers me and pisses me off. Give it to me straight: how long do I have before he gets bored?

I totally understand not wanting to have a one night stand. I don’t think most girls after college especially like having one night stands for fear of backlash or friends silently judging them. I get it. My issue with your question is that this is a single man you’re asking me about. Of course he’s fucking other girls. He’s more than likely having sex with any girl who wants to give it up. Did you not see That Awkward Moment with Efron? Every guy has a roster. Yeah, some rosters are smaller than others but any single male in their 20s has a few girls that he throws feeler texts out to every once in a while.

If it bothers you so much knowing that he’s hooking up with other girls, you have two options: One, you can just stop talking to him altogether and find someone who doesn’t have performance issues. Or two, you can ask him to be exclusive. You should probably have sex with him before you start talking exclusivity, but that’s just my opinion. As for him getting bored? Not happening. If there is even the slightest chance that he thinks you’re going to have sex with him, he will endure as much boredom as is necessary for that to happen. Men will go to unbelievable lengths to seal the deal with a girl he finds attractive. You could sit this guy down and start reading the Encyclopedia to him if he thought there was a chance that it would end in sex. I wouldn’t worry about him getting bored. But I don’t think you’re in any position right now to be mad at him for hooking up with other people. Best of luck. Tell him to cool it with the whiskey-sodas next time you guys are out.

I recently wrote you a question about getting back in the dating game, to which you replied and eventually posted. I am the med school overachiever. Allow me to update you on how that went and how date 2 went tonight.

Well the girl who asked ME on the date turned out to be a senior in college and it was a sorority function. When I learned that this was a sorority function I almost backed out, but i’m glad I didn’t. Shit was lowkey sorta fun. Got really drunk and eventually went home with her. Didn’t round the bases though, no condom and my income outlook is too bright to risk that. Overall, it was a fun night and I wanted to see her again.

This leads me to date two tonight. I was drunk out one night the weekend following our first outing and asked her if she wanted to get food. She obliged. Tonight, we went to a local eatery and I went in on some shrimp and her a salad. From the outside looking in, everything seemed to be going smoothly, and it was. However, having to fill 2.5 hours with never ending conversation is fucking excruciating. You know those nights when you go out to eat wings and drink pitchers with your boys and you can go a solid 5 mins, maybe more, without saying a word? Yeah, that shit never happens with the first couple of dates. It’s exhausting. I hate it.

Am I the only one who hates this? I cant be. No way. Sucks too fucking bad. Does my dating game just suck this bad? Am I the only one who finds filling two hours of eating with endless conversation about her family, and other basic topics unbelievably draining? Am I doomed because I cant seem to get past these first two dates?
I need some help. Should I just continue to do what works, i.e bringing girls home from the bars, or look for something deeper? Do I deserve something deeper?

Wow, looks like we have a little humble bragging going on today. “No condom and my income outlook is too bright.” Thanks for letting me know you make bank, bro. Simple solution there. Don’t come inside her? That’s, like, the first thing you learn not to do when you’re having sex. Do people seriously wear condoms? I’m ashamed to admit that I rarely wear them. I just assume every girl is on birth control and that since there are no physical signs of me having an STD, I’m clean. Probably not the best way to live my life but it’s mine and not yours so back off.

First of all, I never have condoms. One of those things you forget to put on your grocery list and then just never buy. Those things are hella expensive too. I’m a moron, I know. But they suck. And who has the time? Everyone reading this is probably like, “Gross, John. Put a goddamn rubber on you fool.” But I know you’re also all sneaky agreeing with me because even when you do wear a condom it gets ripped off about a minute into sex. Girls hate condoms. Guys hate condoms. Birth control is a hell of a drug. Just saying.

Okay, sorry for the rant on condoms. Let’s get down to brass tacks here. The fact of the matter is, nobody likes going on dates. Everyone who has been on a first date knows about the banal conversations that go on. It’s the same shit every time. I’ve written about it before. What was your major? Thinking about grad school? Where did you grow up? Blah blah blah. It’s exhausting, I get it. But it’s necessary. And everyone has to do it, so stop bitching and just deal. Keep bringing girls home from the bar. Simultaneously look for something deeper. Go to a farmer’s market and try to pick up a nice girl. I don’t know, man. You’re probably in your mid-20s. Enjoy life. We’re all in the same boat as you. You’re not doomed to singledom for eternity. I’m not going to give you the cliché line about someone coming along when you least expect it. Put yourself out there. Suck it up. We all go on shitty dates.

Hi Johnny D,

My name is [redacted] and I’m writing to you because i have a problem. I’m a huge fan of this site and tsm and i read the new articles everyday. Anyway, I thinks you give great advice and i read one of your responses to if guys and girls could be platonic and i thought it was a good response so i thought you could help me. I need a guy’s perspective and since we’re both 24, i might listen more to the advice than i would from a 30 year old. Bear with me, this is kind of complicated.

My boyfriend [name redacted] and i, who is 24 as well, have been dating for 8 months. Everything is great. He’s nice, smart, treats me right, makes me laugh but we haven’t had sex yet. If it was up to me, we would have had sex from the second date, but every time i tried to initiate it, he would clamp up and refuse. After 2 months of this, i lost it and asked him why he wouldn’t have sex with me. I thought he was going to tell me that he was gay but he finally let me know that his parents were crazy religious and they thought sex was wrong and that unless you were using it to reproduce, it shouldn’t be had. Thankfully, he got out of his family situation but the damage was already done.

He feels guilty any time he tries to do anything sexual so he stops himself. I reached out to one of his ex girlfriends from college, who’s a friend of a friend, and she informed me that they would only have sex when he drank too much. It was the only time he didn’t stop her. That sounds a little rapey to me so i’m not going to do that. Adrian has been seeing a therapist for this and she informed me to take things slow and buildup to sex so i have. Around the 5 month mark, after just kissing, i thought why not move to blow jobs. I tried, i fucking tried and he REJECTED me. I don’t know about other girls but i like giving blow jobs. It makes me feel powerful when you see the look on the guy’s face and in past relationships, i have done it frequently. Since he rejected me, i saw it as a challenge and came up with something i like to call, surprise blow jobs- blow jobs at any time and occasion.

There’s a [name redacted] would come home from work blowjob, he got out of the shower blowjob, he’s just dropping off my jacket blowjob and my favorite, hes on his Xbox and hes playing a live game blowjob. The surprise blow jobs worked for a while. One day, i noticed that he was saying, “i shouldn’t be doing this over and over” while i was going down on him. I stopped and he proceeded to drag my face back down until i finished. Eventually he started saying it every time so i stopped blow jobs all together. I felt guilty like i was corrupting him and making what happened to him worse. But the fucked up part is that I can tell he wants me to start again. He will give me this look like he wants me to surprise him. He even brings his Xbox to my place when he stays over because that’s how he received most of them.

So what the fuck am i supposed to do? We can’t have sex. I can’t give him a blowjob because i am starting to hate it. And i need sex. I’m craving it (vibrators don’t work and since i depleted the batteries of one in a month and a half, this is now a problem). I think about how he would feel inside of me and just getting pounded all the time and I’m dying. This is like putting a kid into a candy store and telling them they can’t have anything. It’s gotten to the point where i have thought about breaking up with him. So what do you think i should do? Is our sex life a lost cause or should i hang in there?

Okay this is by far the most fucked up question I’ve ever received. Are you dating a robot? You just told me you throw yourself at this guy on the regular and he’s unresponsive. Your boyfriend sounds like an ungrateful jackass. Blow jobs on top of blow jobs on top of blow jobs. While he’s playing XBox. That’s unreal. I used to have to beg my ex-girlfriend for blow jobs. She hated it. They were few and far between. And you’re handing them out like goddamn Christmas turkeys for the indigent. You should get a medal for putting up with this shit.

My advice for you? Fly the coop. I hate your boyfriend. And how about him saying “I shouldn’t be doing this” while he continues to get head from you? He needs to find someone who has similar views on sex and you need to find someone normal. I can’t believe you’ve been seeing this guy for eight months. Eight months of celibacy? I would have been out of there after a week with no sex. The whole reason you get a significant other is so you can have sex whenever. I hate to break it to you but you should have left a few months ago. You’re just going to build up resentment for him every time he shuts down an advancement from you. It probably doesn’t make you feel very good when you’ve got some lingerie on and all he wants to do is kiss. Wild stuff. Here’s hoping you find someone to have sex with soon. I legitimately wouldn’t wish eight months of celibacy on my worst enemy. Cruel and unusual.

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Johnny D

fashion icon. @dudaronomy on twitter. e-mail:

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