Am I Gay?

But really what is wrong with me?

Anxiety kills dating success. It affects every level of the game: meeting the girl, courting, and sex. In my East Coast, Italian-Catholic, OCD/ADD head, anxiety rules. Most of the time, it simply prevents me from succeeding. But sometimes, after enough events, my mind forces itself to look within to see what is "really going on." This is never good.

Often, I try to examine the fundamental problem I have of being too unaggressive with girls. It takes more than a girl jumping into my bed with me to clue me in that it's okay to at least kiss her. My main fear is that I will move too fast or too early and make her feel like I'm touchy-feely guy. I'd rather look like I'm trying to respect her space than look like touchy-feely guy.

But really — what is wrong with me? Why am I single? Why am I unaggressive? Why don't I try really hard?

A few weeks back I went with a group of friends to see the Broadway production of Young Frankenstein. I resisted at first — for the very idea of sitting in the same place for over an hour is extremely frightening to me. Eventually I settled in, and did a complete 180. The production was grand. Oh, the pageantry! I found myself laughing and tapping my foot along with every number. After a while, I realized that the only two people who were frolicking along with the production with as much zeal as me were the two older gay gentlemen in front of me. As a matter of fact, at times only the three of us laughed at certain jokes.

Does this mean that I, too, am gay? Luckily, I know how my mind works. I no longer ruminate and obsess over things that could be life-changing events or situations. As soon as the play was over, I forgot about my possible gayness and returned to my single life of meeting the wrong girl over and over.

But I did chuckle at the time I truly did fear that I was gay....

I've had plenty of gay moments in my life. When I'm stressed my OCD takes over and I pontificate upon them obsessively. Some highlights:

In the Beginning...

It all started when I was in college and was home on break innocently watching the movie Clueless with my sister. At some point, Alicia Silverstone is all over this guy who turns out to be gay. What startled me was that he did exactly what I did with girls a lot — kind of shied away and didn't go for the kill. This meant, of course, that I must be gay too — if Clueless said so. My OCD demanded that I get confirmation from all trusted people in my life to counteract my thoughts. I approached my mom:

"Mom, what if I turned out to be gay?"

"Well, we'd accept you no matter who you were."

WHAT? That wasn't what I wanted to hear. Had she been expecting me to ask her this, or turn out this way?

James and the Giant Peach (a.k.a. Jenn and Her Giant Peaches)...

I set the unaggressive precedent when I somehow landed the hottest girl with the biggest boobs in high school: Jenn. After making all the guys fall in love with her at a party by killing them in pool and leaning over in her low-cut shirt on each shot, I took her back to her house after promising my friend I'd kiss her goodnight if he kissed his date goodnight. My friend and I would later meet up at Dunkin' Donuts to compare notes.

I got into Jenn's kitchen and froze up under the pressure. However, I did promise my friend I'd kiss Jenn goodnight. I couldn't let him down. I leaned in for a little peck and the girl attacked me. Within seconds, we were on her kitchen floor and she rode me like a cowgirl surveying the Utah prairie. I thought about taking her shirt off for her, but she did it before I could get there. Her giant boobs burst out like bulbous jack-in-the-boxes and I recoiled: What am I supposed to do with those??? Basically, I feared that this girl with the perfect curves would be impossible to satisfy ... so why try? When I finally was able to crawl out to the porch, the girl was staring at me, biting her lip like she wanted to kiss again. I was late to meet up with my friend, so I pointed at the garden and said: "Is that an evergreen?" She turned to look and I slinked off the porch into my car — yelling to her I'd call her later as I drove off to meet my friend. The saddest thing is that my friend, who I went to war for, told me at Dunkin' Donuts that he didn't even kiss his date goodnight because she "got out of the car too fast." Would have helped if he had turned the engine off.

Gay Guys Hitting on Me (and this is in ranked order of effectiveness from worst to best)...

#3 When I was in Italy I was hanging out at an after-hours bar out in the street. I had heard from girls how aggressive the Italian men were. This man definitely lived up to that stereotype. His pitch was:

"Come into alley with me. I give you best blow job you ever have. You will realize you are gay."

Brute force attack really turned me off. Did he think I was some sort of cheap strumpet? No chance.

#2 When I lived in Baltimore, I wrote for a free community newspaper that sent me to a bar to write a review on a singer who was in town. The editor of the paper handed me an address. I went to the street and began walking down the blocks, counting down the addresses. I grew nervous as I got closer and closer to Central Station, the bar my friends and I used to drive by and say: "There's the gay bar!" Finally, I got to the address. Central Station. I called my mom:

"Mom, the bar I'm supposed to do my review in is a gay bar."

"So? They have lives too, and deserve to be written about."

Can't argue with Mom. I got hit on plenty of times that night. The one that stood out was the guy who scientifically tried to break down how he used to be straight and he finally realized that gay was his way. I would be the same eventually, he preached. I appreciated that he wanted to try so hard with me, and that he recognized I needed convincing. Unlike the Italian guy, he didn't treat me like I'd be easy. Hey, I require some effort!

#1 I enjoy looking stupid in pictures (as you can tell). One time my coworkers and I went to a bowling event in special T-shirts (surprisingly, that's not even the gay part yet). The photographer asked me to mug for the camera, so I tied the bottom of my shirt up into a knot like Maryann from Gilligan's Island and made a pouty gay face. Unfortunately, the pictures were posted on our company Website. Fast forward a few months later to the company Christmas party. After the party a bunch of us went to a gathering hosted by Chris, a guy in our Richmond office. As I was innocently grabbing a drink out of the fridge, a perfectly manicured and hair-gelled Chris approached:

"Are you Rich Santos?"


"THE Rich Santos?"

"Uh, yes."

"Are you gay?"


"Are you sure?"

This was an innocent and respectful approach. I've never been asked if I was sure after being approached and hit on by a gay guy. And who knows, maybe the follow-up would work ... but it didn't. Apparently this guy was gay and had seen my picture on the company Website and had gotten "designs" on a little rendezvous.

The Very Good-Looking Italian Soccer Team...

Later in the same year as my Clueless revelation, I went to see the Italian soccer team take on Bulgaria in the World Cup. As "am I gay" rode my mind, I began to notice how good-looking the Italian soccer team was, with their long, dark locks and olive skin. Did I want to have sex with these guys? Or did I just want to be them? It's straight to be able to be secure enough to admit when a guy is good-looking, right? But is it gay to think a guy is good-looking? Before I knew it, the game was over and I had a headache from ruminating about my sexuality.

Eventually, I set up a little table inside my head that worked as a "Gay or Straight O'Meter." It looked a little like this:

Gay: Unaggressive with girls

Straight: Has only gone after girls.

Gay: Can admit a guy is good-looking.

Straight: Can admit a guy is good-looking.

Gay:Hasn't had good sex ever.

Straight:Life is still an endless quest to have sex.

Gay: Scared to ask girls out.

Straight: Spend hours attaining contact information and devising ways to get a girl to go out with me.

Gay: Enjoy the arts and poetry, lyrics.

Straight: But do I just try to culture myself so that I can impress girls?

Gay: Have lots of girls that are friends. I seem so "safe" for them.

Straight: Just about every girl that is a friend is someone I wanted to have sex with at some point.

Gay: N/A

Straight: Never masturbated thinking of a guy, but is this a cover-up?

Gay: Think about girls so much, is it a cover-up?

Straight: Girls confuse the hell out of me and make me think about them all the time.

Gay: Would I be happy sexually and spiritually with a guy instead of a girl?

Straight: Boy, would I miss chasing girls, trying to figure them out, and finally winning someday.

Gay: Love sports, but as a cover-up or because the guys look good in their uniforms and are built athletically?

Straight: Love playing and watching and talking sports.

Gay: I've thought about girls so much that I've run out my brain's supply of cells to devote to girls, so now it's on to guys?

Straight: Still thinking about girls.

In the end, I've developed strategies to master my OCD-inflicted mind. Nature always wins out in the end — all overthinking ever does for me is screw me up.