Chapter 3: My First Three Kisses

Like I’ve already said, I was a late bloomer. I didn’t go on a real date until I was in college, partially because in high school I didn’t have many options. I went to two different boarding schools, and while now I’m pretty open about my life now (clearly), back then, the thought of a teacher catching me doing anything I wasn’t supposed to be doing scared me from doing just about anything most teenagers do. Plus, at my first school all the guys I liked were my older brother’s friends and, therefore, strictly off limits. The second school was so small that by the time I got there, all of the good guys were taken. So, my first kiss came a bit later than others. 

I was a senior in high school and my school was doing “The Crucible” as our Fall play. I was cast as Elizabeth Proctor, and my friend, Jack, was cast as John Proctor. In order to prepare for my role, I decided to watch the 1996 movie version and saw that at the end, right before John was killed, he kissed his wife goodbye. Needless to say, I was both excited and nervous and, being the somewhat manipulative person I am at times, I decided to ask my director if he wanted this to be included, and he said yes. Naturally, I was ecstatic and even though he insisted that it be a surprise, I of course had to tell a friend or two. The director talked to Jack and I about this and after establishing that we were both comfortable with this, we decided the first time we actually kissed would be during our preview before opening night, and it would be a surprise to everyone, including the rest of the cast.

Unfortunately, this also included surprising Jack’s girlfriend at the time, who was also in the play as Abigail. I’d assumed he’d tell her but apparently he did not which (because, high school) turned into a bit of drama for a short time after.

Anyway, I remember being SO careful about everything I ate the day that it was finally going to happen because I was so paranoid about having bad breath. I ran down and brushed my teeth in between scenes probably twice that performance, and reapplied my chapstick and lipstick just before. Finally, the moment was there. I was ready. My heart was racing, but I was ready. But then he started to walk off stage, so I thought to myself, “It’s okay, he forgot, we’ll do it next time.” Next thing I know, he’d run back over and was kissing me — and I blacked out. I genuinely do not remember if I kissed him back (apparently I did), I don’t remember saying my final line, and I don’t remember walking offstage. But it happened, and pretty much all of my teachers, plus some students, witnessed it. My family got to witness one of them, too. I know a lot of people would say that that doesn’t count, but I do. 

Photo by Rodolfo Clix on

My second kiss has a shorter story — while I was studying abroad in Italy, my roommates and I befriended a club promoter named Bryan who used to help us get into clubs and bars. Every time we went out with him, he’d kiss us all good night and he always kissed me on the lips. I figured this was just a European thing so I thought nothing of it until the end of the semester when my roommates and I were reminiscing and one of them said something about him always kissing them on the cheek and I realized that I was the only one he’d been kissing on the lips that whole time. I guess he had a thing for me, and all the free champagne made me not even realize. 

My third first kiss story is, I guess, technically my first real kiss that wasn’t a stage kiss or an unknowing kiss. I was 21, had just returned from Italy, and a friend of a friend had just opened a bar, and I was invited to the opening which meant lots of free drinks and refills which led to not exactly sober Madeline. I had planned on my first *real* kiss being all special and memorable, but it did not happen that way because, well, alcohol. I don’t exactly remember how it happened, but I remember I was talking to some Irish guy (accent and all) and next thing I know, I was having my first real kiss. I don’t remember his name, and I’m pretty positive I told him a fake name, but oh well. At least I finally got the real one out of the way. 

Apparently, this was a pattern for me back in my early 20s when I wasn’t so much of a grandma, because when my roommate and a couple of neighbors and I went to House of Blues for Rewind Wednesday (RIP) during our first CP, I also had a little too much to drink and ended up kissing another Irish guy whose name I don’t remember anymore. I do remember he told me he was in the band at Raglan Road (a restaurant at Disney Springs) and thinking that was so cool and then realizing later he was probably lying. Come to think of it, though, in both of these instances I had to lie and make up excuses for why I wouldn’t go home with them. I guess “no” doesn’t always mean no for some Irish-men? 

At the time of all of those first three, I remember being disappointed that none of these were a movie style foot-popping kiss (name that movie), but now I realize that honestly, none of that matters. A kiss is a kiss, and I like my stories better than I thought I would. They make me, me, you know? 

Since then, I’ve had a lot more kisses… some good, some bad. If I had to pick a worst kiss, well, I don’t want to be mean and name them, but let’s just say it wasn’t too long before I decided to start this. It wasn’t a technique thing as much as it was that really, we just didn’t have great chemistry. Best would be Sam or Dave (all of whom you’ll meet in later chapters). I’ve yet to have the “foot-popping” kiss described in “The Princess Diaries,” but I’m sure it’s to come. 

Hopefully, I don’t have to kiss too many more frogs before it does. I think I’ve kissed enough of those. 

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