Cradle Robbing

Sometimes dates are the culmination of years of planning.

Names have been changed to protect the barely legal.

Name of Date: Jail Bait
Date #: 1
Looks Like: Tyson Ritter's younger brother.
Age: 18
Occupation: Student
Where we met: I was on the production crew for a show where he was in the cast.
What Happened: So I met Jail Bait when he actually WAS Jail Bait (16). The first time I saw him I thought "Oh my gosh, that kid is the most adorable thing I have ever seen on the entire planet." Thus the seed of a crush grew. I avoided him though to avoid any temptation/jail time. But over the next couple of months we became friends and his friends revealed to me that he "was in love with me, you know?" I was flattered but even that poetic confession of undying affection wasn't enough to sway me.

I still thought about him from time to time over the next couple of months and decided that when he turned 18, I would definitely take him on a date. I made this known and he hungrily agreed. In fact the day he turned 18 he facebooked me asking when our date was. Adorable, right?

Well we made plans over the next couple of months. Seriously. Planning this date was like planning an effing wedding. Where should we meet? Should I pick you up? What if it rains? Maybe we could do this? Back and forth for like ever. Once plans were finalized though, I knew it was go-time.

We met up for Japanese food and he walks in wearing absolutely precious salmon colored pants. Its a bold choice, but he worked it. He is confident enough to pull it off. This is normally something I'd judge the hell out of. I'd be all "um banana republic wants their $98 chinos back, bitch." But like I said, he doesn't look like a WASP-Y douche.

We talk about what we've been doing since the show(s) we worked on and its really nice to catch up with him. Despite our age difference (somewhere between 5 - 7 yrs. ugh.... i know.) we have a lot to talk about. and when we're done eating I don't want it to end.

I quickly suggest we head back to my place to have an indoor picnic and watch the rain. Romantic, right? I'm kind of awesome at these things. So I spread a blanket out and open the blinds and we watch the rain. I also put on my "make-out" mix on my ipod. Yes, ladies and gays, I have a make-out mix on my ipod. Don't be judgin'... you do it. Music to get it on to. A lot of acoustic guitar and syrupy lyrics. (Thank you John Mayer and DMB!)

So the music is playing. We're watching the rain... and nothing is happening. All that is left for me to do is wear a hat that says "Times for the make-outs now!" He just isn't getting the picture. So I actually say:

"You know I think you're cute right?"

"Yeah..."

"You know I want to kiss you right?"

"Yeah..."

"Would that be ok?"

and Jail Bail shrugs. He SHRUGS!... which i take as a yes. So I lean forward and begin my awesome art of kissing. I'm like really good at it, p.s. You can ask like literally dozens and dozens of people. Most of you reading the blog have kissed me and are nodding your heads right now. Don't lie.

So we pause and I can tell he's nervous. Shaking. And I ask if he's ok and he says "yes... its just..." and my mind freaks out. "Its just what? You're really only 17? You have a boyfriend? You don't like me anymore?"

"Its just... you're my first kiss."

I was stunned. This kid is gorgeous and I'm his first kiss. I feel like a champion and the biggest creeper in the world. On the one hand, lucky-ass him for getting his first kiss from someone as awesome as me. On the other... it probably should have come from someone he could have had a real relationship with. I don't know what to do. I ask if he wants to stop. He says "...no" and basically tackles me.

We end up making out for another 30 minutes. I really want to take his clothes off... but I'm not that terrible. When he leaves I tell him I'll see him at his HS graduation... god, i'm such a creepy perv.

Gained Points For: Picking up the technique really quickly

Lost Points For: Making me beg for it. I gotta keep some dignity, you know?

Mistakes I Made: um... .GOING ON A DATE WITH AN 18 YEAR OLD?!?

Chances for another date: Probably not good. He is going off to college and will find a candy store of young hot gay boys there. I'll be the last thing on his mind. However, he is so adorable and technically its legal so... I'd be up for it.

Overall Grade: B