Though I've never lived in Long Island...

I was a Lolita.

Twice.

I was 14 and a sophomore in high school (had a late birthday) and met a much older boy. He was 22. (With just the right make-up and padded bra I could make myself look a LOT older.) I went to an ultra conservative super preppy Catholic school about 45 minutes from where I lived and needless to say it didn't really fit my personality or lifestyle. I preferred to hang around my public school friends who lived much closer and were a bit more liberal in their thinking and behavior. That's when I met the man. He told me he was 18 and I told him I was 16 so for a while we didn't seem like too much of an odd pair. While we were at a drive-in movie, watching Dirty Dancing (how fitting!) I reached into his pocket and pulled out---his LICENSE (perverts!) and that's when I saw his birthdate. It was then that I told him my real age and for about 30 minutes straight, all I remember him saying was "NO WAY! NO WAY!! NO F*CKING WAYYYY!!!!!" We both realized there was just way too big an age difference and it wasn't a good idea to continue seeing each other. Now, for the record, no deed was done, all we had ever done was kiss. I'm 100% serious about this.

So we decided that we couldn't see each other anymore but we still talked on the phone EVERY single night and even wrote letters and cards to each other. It was weird. I probably act more immature now at 35 then I did at 14 and that's why the "friendship" continued to evolve. We realized after a while that we still enjoyed each others company (and hell, he used to let me drive his car, even without a learner's permit!) so we started to hang out again.

I remember one afternoon he drove me home from school and my mom wasn't home. We sat in the family room and watched MTV and this video came on. Cheezy, I know but during the video we started to kiss and things got a little heated. The part of the song where it goes, "I don't want to touch you too much baby, cuz, making love to you might drive me crazy" was playing and he stopped kissing me and freaked out and said he couldn't do this anymore. He got up to leave and told me that he was afraid he would end up in jail. I had no idea what he was talking about. I never even realized that the age difference was actually illegal. He told me that we just couldn't see each other anymore. And he didn't want to talk or write letters or anything. He left my house (with blue balls) and I sat on the couch confused. Why the heck would he go to jail?

Later that night, he called. He asked, "How many people know my REAL age?" I told him nobody did because I knew they would tell me I'm crazy, so everyone thought he was still 18. He said okay let's keep it that way, no matter what never tell anyone I'm 22. Ok, ok.

So we continued to "date" for a couple more months and by now I had turned 15 which meant he also turned another year older. He would send flowers to school and write me songs (he was in a band) and for a silly teen it was pretty flattering.

Until I met...another 22 year old.

This time, it was a professional baseball player. And we dated (long distance) for almost a year. He thought I was 18 (because that's what I told him) but I blew it when I started school the next semester and told him I was taking Driver's Ed. He said, "WHAT??? Why so late??? Is the law different in Illinois?"

Woops.

The funny thing is when he would come into town to play the Cubs (he played for Cincinnati) he would have a car service pick me up at home and bring me to the games. He was very much a gentleman, and he wouldn't have wanted me to drive down by myself anyway. So he really never thought to ask me if I could drive so the subject never came up. Until I opened my big fat mouth.

There's something incredibly liberating about sharing this on my public journal. I may just start to purge all my scandalous secrets on here.

I still think my best dating story dates back to when I was 21 and dated a 36 year old bi-sexual model. DAMN was he hot! And so was his boyfriend.