“I Think He’s Gay” And Other Thoughts On A Date

It was an odd night.

For fun, I tried something new with dating. I decided that I’d say “yes” to anyone who asked me out. Fuck it. I needed the distraction during the nights away from my kids and the bar is low.

Buy me dinner and call me pretty. That’s it. That’s the bar.

I haven’t written about them because they’re generally boring. There was the guy who bragged about his immense wealth. There was the doctor who was so small, that my 100-pound frame was able to wrap itself around him during a hug. There was the date with the lawyer who kept rubbing my ears when kissing me, expecting a genie to pop out.

Then there was Caleb.

Homeboy was hot. Most guys take dorky pictures and one must weed through their stunted selfie game to determine a guy’s true appearance. Caleb was fit, blond, blue-eyed, and had enviable teeth.

We texted for a while through the dating app. My lesson learned is to stick with the app as much as possible because when it’s time to bail, it’s a lot easier when they don’t have your phone number. Finally, he asked me out.

I offered to swing by his neighborhood since my town consists of a car wash and a Del Taco. Caleb suggested a lounge-y place near his work. He was a bigwig financial director for an auto dealership. In SoCal, it’s odd to find guys who still wear suits to work.

My company was hosting a party for the return to the office but I bailed on it so I could get cute-ified. I would have eagerly ditched that party for a root canal. In a post-Covid life, free appetizers aren’t enough to make me stay after hours to talk to people I’d never hang out with anyway.

When I get ready, it’s hit or miss if my face will cooperate. Here’s the thing with makeup: you could pick the same products every day for a month and it would still be a craps shoot if it’ll look wonky or great. I buffer in extra time with pre-date makeup in case I need to wash it all off and start over.

This time, my makeup was flawless. Adding a form-fitting, spaghetti strap red sundress and I looked bomb. Why don’t I ever look this good when I’m with friends who post endless pictures on Instagram? On a typical day, I look like a goat who was punched in the face.

Parking at the lounge was tough but I lucked out when I pulled in. Caleb pulls in shortly after and circles the lot, looking for a spot. He sees me and does a head nod. He’ll have to park across the street. Most guys in this scenario would roll down their window and ask if I want to hop in or at least say hello. Caleb simply drives off, leaving me wondering if I even got the right guy.

I wait as he parks his white, convertible Mercedes. After some time, he treks back to the restaurant.

Caleb’s outfit was…questionable. I didn’t expect him to show up in a suit and tie from work. But it’s a date. A nice t-shirt and non-stained jeans are more than fine for this West Coast lifestyle.

At first glance, it looks like he’s wearing black sweatpants. As he gets closer, I discover they’re more of a Hammer Pants/Sweatpants/Cargo Pants hybrid.

Caleb’s t-shirt is faded black with a front pocket. The front pocket had pictures of bananas on it. Not just one banana. Multiple bananas on this faded, dingy t-shirt.

With Caleb’s bizarre black track pants and a grungy t-shirt came no socks with his shoes. Specifically, brown loafers. I believe that look is what’s considered Yacht Attire. On a boat, you need sensible shoes but remove socks to give a flip-flop vibe.

Overall, he looks like he’s ready to clean some gutters and mow the lawn.

When Caleb opens his mouth to greet me, I’m stunned by his voice. It’s extremely high-pitched and flamboyant. I’m not talking Justin Timberlake. Think RuPaul’s voice cadence when he’s in drag. It takes me a second to register the sound of his voice against his appearance.

We sit at the lounge bar and begin chatting. He opts for a non-alcoholic beverage because he’s on a health kick. Why suggest a lounge if you don’t have alcohol? I specifically only date people who drink. Having already ordered a glass of wine, I feel like a douchebag.

At one point I comment on how his life must be rough given his appearance. “Is that your way of telling me I’m good-looking?” he asks. I confirm that he knows he’s incredibly attractive. Most guys go bonkers for physical compliments because they’re not readily given the way women receive them. Compliments slide right off Caleb.

Nowhere during the evening did he make any physical contact with me. I occasionally touched his arm when I laughed, trying to break the intimacy wall. I’m floored he hasn’t touched my back or put his hand on my thigh.

Halfway through the date, I tell myself that there is zero chemistry and I’m not sure he’s straight. But hey, I’m cool having another LGBTQ+ friend. Let the record show that I’m not assuming he’s gay just because he’s not physically into me. I know I’m not everyone’s cup of tea.

The check arrives from my glass of wine and the two appetizers we ordered. Caleb is vegetarian, which is enough of a deal-breaker. I need a dude who will devour an animal carcass while I gingerly pick the red peppers off my food because only I can be a picky eater.

Caleb walks me to my car and asks if he can finally have my phone number. Fuck. I hoped he’d ask for it later via the dating app, where I could respectfully shoot him down. I give him my Google Voice number instead of my regular one.

It’s the end of the date. I don’t remember the last time, if ever, that the end of a date has been awkward. While there’s anticipation for a kiss, every guy goes in for the moment if they haven’t already done so during the date.

Caleb leans into me and puts his arms around me.

I reciprocate the kiss.

Except he wasn’t going in for a kiss. He was going in for a hug.

I smack my lips midway between his cheek and his lips. Epic fail.

“Oh, you were expecting a kiss?” Caleb asks. Yes, bro, you asked for my phone number so I assumed you were into me enough to try for a standard kiss at the end of the date. Why won’t the ground open up and swallow me whole to put me out of my embarrassment?

After I sheepishly confirm, he goes in for a real kiss. That’s when the night does a 180.

Suddenly, Caleb is an alpha male ready to devour me. He kisses me passionately, repeating how sexy and hot I am. “What the actual fuck is happening with Mr. Yacht Shoes?” I ask myself.

I try to end the date but etiquette says I should drive him to his car since he walked me to mine. “Do you want a ride to your car?” I ask, hoping he’ll decline. Caleb replies, “You know what will happen if we get in the car, right?”

Umm…no. I don’t. More making out?

We sit in my car and he kisses me some more. I eventually pull away and turn my car on to begin driving. Hammer Pants Man is having none of that and pulls me in for more making out. For a guy who didn’t touch me once during the date, he’s compensating now. His hands are up my dress, rubbing all up on my girly parts. He pulls my dress down and plays with my nipples. He’s on loop repeating how hot and sexy I am.

On one hand, this aggressive side is great. On the other hand, why does this feel like a completely different person? I run my hands along his stomach but stop short of rubbing his dick through his freakishly weird pants. I’m ready to start the car and get the fuck out of there.

“Oh, you were so close,” Caleb says. He means that he wants me to touch his man meat. I just want the night to be over so I decide to do what’s easiest: disarm his weapon with my mouth. Yes, I’m rewarding somewhat bad behavior but I don’t care. I just want to go home.

While I’m going to town between his legs, Caleb mumbles about how badly he wanted me and more of the sexy/hot talk. I pause mid-blow to say, “Really? I was positive that you have me in the friend zone all night.” It’s probably the most unsexy thing I’ve ever said when giving a guy a blowjob for the first time. Yes, I’ve said very unsexy things on subsequent blowjobs.

Thankfully, he finishes quickly. Now we’re chatting flirtatiously the way it should have been the entire date. He makes me laugh. He makes fun of his “douchebag car”. He tells me I have the sexiest moans when he’s touching my body. Where was this guy all evening?

As I drive away, I briefly consider giving Banana Tshirt Man another shot. My instincts tell me it’s not a good fit. Not just because he gave me friend vibes all night or because he dressed like a homeless guy. Not just because he’s vegetarian. Caleb also believes in the Mayan calendar and that the world did end in 2012. The red flags are blinding.

I make a quick pitstop at the grocery store for milk before going home. A guy walks past me and says, “Nice dress”.

This stranger and his one comment had more chemistry with me in a split second than I did on an entire date. That’s when I knew I wouldn’t see Caleb for Date #2.