Questions From The Chase: Potential Lesbian, A Virgin, And A Snake In The Grass

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Questions From The Chase: Potential Lesbian, A Virgin, And A Snake In The Grass

Holy shit. I got some pretty heavy questions sent my way recently and did my absolute best with them. I think these have been the most challenging to answer since I started this segment. As always, keep the questions coming my way. Inquiries are below in quotes.

Hi Johnny,

I need your help. I have a problem and I thought I should send you a message. Btw, I had to scroll through your articles on pgp till I found one that had a link to your email address to write you. I didn’t know if there was another way. Also, this is a fake email address because I would die if anyone found out about this.

So I fucked my best friend “Julie” and I’m so confused. This wouldn’t be such a big deal but we are both girls. Julie and I have been best friends since we were 8. We went to the same school, the same college and even found jobs in the same city so we would be together. We have so much in common and she is like a sister to me and I don’t know what I would do without her. Anyway before we hooked up, I was going through a bit of a dry spell. I was getting over a cheating ex and I had no desire to jump onto another dick that was bound to be full of disappointment and lies.

Last week, Julie and I decided to have a girls night in full of alcohol, chick flicks, and bad food. It was great but when I drink alcohol, I get horny to the point, it’s like Niagara falls down there. Julie knows me and we have talked about our sex life to each other that she knows alcohol is a trigger for me. She saw the change in me and we just started talking about sex while doing more shots. Eventually, we were wasted and next thing I know, we’re kissing and I’m not stopping her. Julie has experimented with girls before and had relationships with them but I haven’t. I went with the flow and eventually clothes came off and before I know it, her head’s between my thighs and I’m screaming her name. I reciprocated and it was great.

I woke up the next morning and I immediately regretted what I had done. Julie woke up and just acted like everything was normal. Since she didn’t say anything, I didn’t either and we went along with our day. Even though we haven’t said anything, things have changed. The looks we give each other sometimes aren’t fully platonic. I used to undress in front of her all the time but now, the way she looks at me, while I do, is different. She will also hug me a little too long or she will touch me in a flirtatious way.

Little things like that are confusing because I thought I was straight. I mean, I see half naked girls in the gym all the time and I feel nothing but I see her half naked and it just makes me want to jump her bones. I told a friend about this and she said, since we are both single, there’s no harm in seeing where this goes but this is my best friend. This is the person I plan on having a friendship with forever. I can’t risk a friendship of over 14 years over a hookup. What if she wants more than I do.? What if it ends badly? What if one of us meets someone and the other gets jealous?

Basically, I’m kind of against pursuing this any further and I’m planning on ignoring everything till she stops. But am I reading too much into this? Would it just be harmless fun if we made this a regular thing? I really do miss her face between my thighs. Anyway, what should I do?

Before I write any sort of response to this, I’d like to preface the following with a word to my feminists and over-reactors out there: this question was sent to me. She asked for my opinion so please leave your pitchforks and torches at the door.

I can’t sit behind my laptop and give you a definitive answer on whether you’re straight or not. Don’t most girls “experiment” in their early-to-mid-20s? Like, I’ve seen countless girls makeout with each other at bars and parties, although I guess it’s a little different when you’re eating each other out and screaming your best friends name out loud. That’s intimate on an entirely different level. You said you were really drunk, but maybe try it again sober and see if you still like it? It sounds like you enjoyed it, and there isn’t anything wrong with exploring another womans body. I would play it out and see where it goes. If you liked it, why fight it?

John, I don’t know how else to say this so I’m going to be blunt. I’m a 24 year old virgin. Yikes, I know. I’m not saving myself for marriage but I’ve never had a steady boyfriend. I’ve had plenty of opportunities but I want to be with a guy who really cares for me. The older I get, the more worried I get. The movies make it seem like every guy is dying to be with a virgin but I’ve gone out with guys who wanted nothing to do with me after finding out. How do guys really feel about virgins? Help!

Yikes. A 24-year-old virgin? I’d like to tell you that someone will jump at the opportunity to have sex with a virgin but we’re not living in medieval times. It’s 2016 and people want to jump into bed with people who know what their doing. I can’t honestly tell you that there are a ton of people who want to be with virgins. The inexperience, the pain (for you), and that stupid cliche about virgins being clingy are hurdles you’re going to have to get over. I would never have sex with a virgin. Being someone’s first carries too much weight and I’m pretty sure every girls first time is incredibly painful. So that’s a big no for me. Maybe you should try and find another virgin that will do the deed with you? I don’t know. I’m honestly stumped here. You’re in a very shitty gray area. Like, you’re still very young. So as much as I think it isn’t a big deal for a 24-year-old to be a virgin, it also is kind of a big deal in this day and age. Twenty years ago, nobody would have batted an eye about that, but like I said, it’s 2016. You’re behind the 8-ball. I guess the best advice I can give you is too keep on keeping on. Good luck out there, I hope you get laid soon.


Love your articles and advice about the chase. I need your help ASAP. This is kind of a long and conveluted story, so I apologize in advance. I met this dude off of Bumble back in February and we’ve really hit it off. He’s met all of my friends, I’ve met all of his, and we spend just about every weekend together as well as at least one weekday sleepover per week. We’ve drunkenly had the DTR talk 3 or 4 times, but niether of us really came to any sort of conclsion, but we both agreed we weren’t seeing any other people. I can honestly say that I haven’t which is pretty out of character for me. I’m the type of girl to bring a different guy home every weekend, even when I’m just causally seeing someone. What can I say, I like sex. Anyway, I come to find out that he hooked up with another girl. When I confronted him about it, he lied to me three times. It went from “It happened once when I was fucked up” to “We have mutual friends so I only ever hang out with her with a big group of people” to me finding out she had been at his house earlier that week. I made it very clear that while it sucks to hear he’s been seeing someone else, I’m just mad that he lied. He was very apologetic, came over, brought flowers, ect. The next day I went on vacation and here is where it get interesting: His best friend and his best friend’s girlfriend happened to be vacationing at the same spot as me. I had been drinking on the beach for a couple of days and when they got there a few days later, they wanted to come out with me and my friend. After too many tequila shots, a lot of dancing, and some naked swimming in the ocean, I had a threesome with my dude’s best friend and his best friend’s girlfriend. I’ll spare you the details, but it was amazing. So my question(s) for you: Do I pretend like that never hapened and keep seeing this guy? Can I trust this guy? Does this guy even like me seeing as how his best friend thought it was okay to put his dick in my mouth? Help.

I apreciate any insight you have for me.

Yeah, you’re fucked. This is some serious snake in the grass shit. I mean, yeah, I get that you’re upset about this kid fucking someone else and then lying about it – but you went and fucked his best friend? You couldn’t find anyone else? Even if you didn’t tell your Bumble friend about your threesome WITH HIS BEST FRIEND, you realize that his best friend is going to tell him, right? Any shot you had at a legitimate relationship got thrown out the window the second “his best friend thought it was okay to put his dick in my [your] mouth.”

I legit wanted to throw up after I read your submission. If a girl came back from vacation who I have been seeing and told me that story I would have puked all over her. I can’t even believe you’re asking me if you can pretend like this never happened. Your Bumble bro is going to find out about this. There’s a common practice used amongst politicians, celebrities, and athletes when they know a negative story is about to hit the presses; it’s commonly referred to as “getting ahead of the story.” If you really want to come out of this thing looking halfway decent, tell him yourself. Don’t wait for his best friend to break the news to him. If it were me? No chance I’m ever talking to you again. If you make a man choose between his best friend and girl who they have both been inside of it’s a no-brainer. You’ve made your bed, now lay in it. Time to hang the cleats up with this one. Any way you play this out, you’re coming out on the losing end. Sorry, but you shouldn’t have fucked his best friend. That’s pretty ruthless, even for me.

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