What Separates Men From Boys

The following is an excerpt from a text conversation I had earlier with a guy I was seeing for a few weeks. The back story: he's great on paper -- smart, funny, has a great job, owns a car. In practice however, he's rather timid, somewhat shy, and incredibly awkward, which I found endearing... until I didn't. He has a big dick, he lasts a long time, and he knows how to use it and his fingers, but not once in the handful of times we had sex did he so much as attempt to take his mouth anywhere below my chest. He also nearly cried when there was a little blood on the condom once. Definitely wasn't going to work.

Last night he started asking me for dating/girl advice, as when I broke it off with him I told him "I think that you're perfect for someone, it's just not me," and as all nice guys do, he wanted to stay friends. He's tried a bit of online dating that's led to nothing, and he doesn't really know how to approach women IRL, but he says that with his new great job, he's finding himself wanting to settle down more and more, (keep in mind, still lives with his parents. Settle in the basement? I don't know.) He's also decided that he wants to date older women. Right.

I gave him some tips, and then went to meet my friend for a few drinks. He texted me more while out, and eventually I felt that this was the appropriate response:

Me: Alright, I'm going to give you the best advice you'll ever get: IF you are going to try dating older women you're going to need to get over your fear of blood, and you're going to need to start going down on them - and I mean that honestly for your own advancement, and in no way as an insult.
Me: Not necessarily at the same time.
Him: I had 2 gut-wrenching experiences in that department, so I'm not sure
Me: In which department?
Him: Going down...
Me: So? You think your spunk tastes like jolly ranchers or something?
Him: I don't know.
Me: Well, it doesn't.
Him: Okay
Me: It separates the men from the boys. And women want men. Otherwise you may as well stick to dating teenagers.

Asking a boy out IN REAL LIFE

As someone who has no problem asking someone out via text or email, I have a super hard time asking someone out in person. IN REAL LIFE.

After a sex free period of 2.5 months, due to seeing a man with morals and also being in a general funk, I have found myself getting back to my slutty ways.

This Saturday I have a date with a latin man I am hoping to ravish, on Monday I have plans for beer and fooseball with some other dude, and then on Tuesday I am going for coffee with a highschool teacher.

I am excited for these outings and am glad to be getting out there again and meeting new people but these guys are not the ones I am REALLY excited for....

I work in a store that sells cool gift stuff and although most of the customers are women, we do have a few men come in from time to time. Lately there has been one male customer who has really stood out to me.

I don't know his name, but everytime he comes in I make sure to help him and we spend a lot of time chatting and there is some flirting. The last time he was in I was really awkward and flustered because I realized I had a crush on him and I really wanted to do something about it. I resolved that the next time he was in I would ask him out.

Cut to yesterday.

He walked in the store and we locked eyes right away and I couldn;t help myself from grinning really happily at him and I got a really big smile in return! We chatted a bit and he showed me pictures from a recent trip to Asia. We flirted and I tried to be cool and not get flustered like last time.

I knew I had to be proactive. I was going to do it. I was going to ask him out. Fuck, I was nervous.

I was alone behind the counter for a minute, getting his items ready to bag. He was walking towards the counter. I realized other people were walking towards the counter too! If I asked him out there would be an audience!

MOMENT OF PANIC.

I quickly grabbed a piece of paper and scribbled down a note with my name and number and taped it to the largest item in his bag.

It felt like chickening out and I regretted it as soon as he walked out. I considered following him outside but I had already felt kind of resigned.

Because it's Christmas and the things he bought were gifts he probably won't look in the bag until December 24th and I am worried that he might feel like it's too late or something....

GAWD. WHY DIDN'T I JUST SUCK IT UP AND ASK HIM AND FIND OUT THEN AND THERE IF HE IS SINGLE OR NOT?!

Now I play the waiting game. Maybe I will get laid by the latin man in the meantime.