Are You Friggin' Kidding Me?

One Bostonian's Misadventures in Dating

The Over-Sexter


Because I love the guys over at Singleosophy so much, I decided to randomly agree to go out with a guy without the usual screening that I do. And when he got crazier and crazier, I let it go and didn’t cancel the date, just for the sake of this blog. Let’s get into it.


So, I clicked to meet this guy on the OKCupid app and he agreed rather quickly. We started messaging a little on the app and he asked for my number. Right off the bat, he was pressing for information about my sex life. I tried and tried to keep him at bay. We decided to meet up Friday night after I got back from the gym.

I told him off a few times Thursday night, when we first started chatting. He was trying to flirt, but being way too obnoxious. When I wouldn’t give up any info. I was ready to give up on meeting him, but I decided that I would just use this as fodder for my blog.

But it wouldn’t stop.

He texted me all day Friday while I was at work. Trying to get me to sext with him and whatnot. Finally, I broke down and said the following:

Well, this worked against me and he pressed for more. So, I gave in and gave him what he wanted. I sent him the dirtiest text messages, in hope that I would scare him off. And guess what? He did have to leave work for a little bit.

So after work, I went to the gym for a few hours. I actually had a really hard class and was hurting quite a bit. I was thinking about cancelling just for that, but I thought I’d at least see what was up. He ended up texting me and we got to talking about how the night was going to go and what the plan was. He started annoying me again and I told him that I didn’t think I wanted to meet up with him if he was going to be all awkward about it. He agreed and said he was embarrassed to meet me. So then I let him have it:

We never went out, THANK THE LORD. And he did try to message me later on, but I ignored it. I’m glad I can drink this one under the table.



Author: Jane Champagne

I'm a single late 20s chick, living in Boston. I go on a lot of horrible dates, but some good ones, too.

12 thoughts on “The Over-Sexter

  1. Lol some guys are ridiculous and most definitely take things too far!!! At least he’s self perceptive – he acknowledged the fact that he’s retarded. Haha. Even though this didn’t end up being a date, it was definitely a funny thing to read!!!

    • Yea, I’m glad that it happened, just to have something random to write about. I have a few more stories to throw in here soon. And yea, the guy is a complete idiot. Ugh. haha

  2. Ugh I hate the sex chat before even meeting. Like seriously, talk about making it awkward for first date small talk….. Love changing guys names in my phone. There is one that I named “Ass licking liar” about a year ago, he still texts every so often and actually seems quite nice. I can’t remember his name or what he lied about!

  3. I can’t help but think that the guys who are requesting all this personal info are only looking for the booty call. I was considered quite forward, 100 yrs ago, because I asked a guy out instead of waiting for him to ask me. I just don’t get the rush to these details, unless u are only out to get laid. But aren’t ther specific filters for that?

    • I agree with you! I’ve been pleasantly surprised with The Engineer, as he doesn’t seem to be looking for a hookup, but did bring up sex a little early. Usually, the guy is just looking for a hook up when they bring up sex so soon. I’m glad I was never serious about this clown.

  4. And guys wonder why women have such low opinions of us all.

  5. We love you too, lady! Andy I think I can speak for the rest of the crew when I say that we appreciate you seeking interesting stories. This post got my analytical mind working, JC, and I have some thoughts. Look forward to a response post on Singleosophy.

  6. Pingback: In Re: The Over-Sexter « Singleosophy

  7. Pingback: More on The Over-Sexter « Are You Friggin' Kidding Me?

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