Missed Opportunities

We all have those moments from our past that we reflect on from time to time. These are 3 of my oldest memories.

Opportunity #1

Lexi was a close friend’s cousin. She was a 10 before I knew what a 10 was. Both of my close friends, who I believed had a better chance with her, also had their sights set on Lexi… and yet she expressed her interest in me. I was the luckiest guy I knew, but also the most anxious. I was so afraid of screwing things up, I broke up with her in a very short amount of time. I realized my error and tried to unfuck myself but she wasn’t having any of it. Lexi was the first girl I remember attempting to french kiss and then bailing at the last second because I was too afraid. I don’t remember if we ever did fully kiss that way.

Opportunity #2

Leia was tall with short blonde hair and an athletic build. Leia had amazing features that I enjoyed checking out as often as I could and in no particular order. Again, myself and most of the guys I knew all had crushes on her. By high school she and I were somewhere between acquaintances and friends. 

One day she pulled me aside and told me she knew I smoked out from time to time and wanted to try it herself. For some reason I was the only guy she trusted enough to do something like that with. 

To journey into an altered state of mind while alone with Leia? You better fucking believe I was going to honor that request, even at the risk of her boyfriend finding out and kicking the shit out of me -which I knew he was more than capable of doing.

The day arrived and I drove to her house. Part of me expected to see her boyfriend there, but was extremely happy to discover she and I were indeed alone. We ventured into a small building behind her house and before we sparked up, she asked about how to smoke it. I crafted an answer made of partial truths wrapped in my underlying desires. 

To keep her from accidentally ruining the joint with wet lips or burning her fingers, I graciously offered to shotgun the smoke to her. I’d take a toke, we’d lock lips, then blow it into her mouth as she inhaled. We would also do small hits instead of larger ones in order to keep it from burning her throat.

She agreed and we were on our way to peace and love… Or at least high as kites. I lit up, took a hit and moved towards her. She responded by leaning in to me… and my mouth touched her skin for the very first time. It was excruciating bliss. 

With each passing of the smoke, I would close my eyes and fantasize about actually kissing her. As we went along, our inhale/exhale timing continued to improve. The physical sensation of emptying my lungs into her mouth and simultaneously feeling her pull the air from my body into her lungs was damn near sexual to me. My insides were trembling from the amount of restraint I was commanding. The smaller hits were designed to minimize the chances of it making her cough, but also maximize the number of times I got to pseudo-kiss her.

Once we burned it down, we swaggered back into her house to allow our buzz to settle in. Of course her boyfriend called just after we were thoroughly baked, which spun me into paranoia the entire time they were on the phone. She confirmed he wasn’t coming over and was at work. That was a major relief.

Leia called me into her bedroom and we stood around for a few minutes talking about random things. I had no idea if we were just chililn’ or if she was executing an agenda. My mind was screaming to make a minor advance, but I could not get myself to do it. I felt she asked me to smoke with her because she trusted that I wouldn’t try anything once she was under the influence, but most importantly, I had zero faith in the idea that she could have found me of interest. She was hot AF and could have had any guy she wanted. I checked myself and steadied my lustful thoughts.

We floated back to the living room. She laid down on the couch. I chose to lay on the floor in front of her. We both stared at the ceiling. From time to time we’d have random conversations. 

Maybe 20 minutes into vegging-out…

Leia “Can I ask you a personal question?”

Me “Sure. Fire away,”

Leia “Have you ever thought about being with me?”

Me “If you weren’t with Doug, absolutely.”

Leia “I see…” (She lets out a sigh)

Was that a good thing? A bad thing? Was she hinting that she wanted to fuck around and I blew it because I mentioned her boyfriend? Was she disappointed in the fact I was attracted to her for more than a friend? I was too afraid to ask for clarification. I wanted to hear the answer but only if I knew I’d like her response. I would’ve totally accepted an ass-kicking if it meant I got to hook up with Leia… but I never bothered to find out. I stayed for a little while longer and then left. We neither talked about nor repeated that day again.

Opportunity #3

The same friend who set me up with Lexi, convinced me to ask out my third missed opportunity… Denise.

Denise was with a cheerleader from another school and was one of the most visually stunning girls I had ever seen. She was somewhere around 5’5”, long golden blonde hair and smoky blue eyes. She was a cheerleader, so of course her body was everything guys think about when visualizing a cheerleader’s body.

To my amazement, she said yes. I freaked the fuck out. Smoking hot cheerleaders had no business agreeing to go out with me. What did girls like her even enjoy doing?

I wanted to impress her in the most sincere way possible. I didn’t know what a traditional date was for people our age since most guys I knew were about getting drunk and having sex. The last thing I wanted her to feel was that I was taking her out so I could sleep with her.

Did I want to sleep with her? Of fucking course I did. Believe it or not, I had more of a desire to spend an evening getting to know a beautiful girl and finding out if a girl like Denise could find an interest in a guy like me. I gathered all my courage and sat down to devise a complete date.

I arranged dinner at the restaurant where I worked at the time. It was an upscale place that was on the pricey side, but my employee discount made it affordable. Plus I wanted to show Denise off to my coworkers. They were impressed -so much so that a guy I worked with came out, sat down and pretended to flirt with her in front of me.

After dinner, I escorted my date to the docks where we boarded a vintage steamboat for a nice evening cruise. Denise was very personable, kind, and sweet. I enjoyed every second of my time with her and didn’t want the date to end. She was a collection of so many things I was not, my fear was that I was looking at something I would never be able to have for myself.

Initial rejection may sting, but at least we get to throw ourselves a lifeline by saying “they don’t know what they’re missing.” Rejection after they’ve spent an evening with you cuts tremendously deeper because it says they’ve seen what you have to offer and chose to pass.

When the boat returned to the dock, our date was at an end. We walked back to my car and I drove her home. Her house was empty when we pulled into the driveway. Denise invited me in. She led me to her room and that’s when desire and self-esteem went to war. Had she been less perfect, I would’ve made an attempt. There was a little tension in the air, but I read that as mutual nervousness. What I really wanted to do was throw her on the bed and go down on her until we were both dehydrated… Instead, I thanked her for the date and then showed myself out. The whole drive home I kicked myself for not at least trying to give her a small kiss… Something… But fear and the desire to not treat her like a piece of meat had once again held me back.

There was no second date and I don’t remember ever talking to her again after that. I never knew if she was insulted or thankful I didn’t try something. Maybe remembering it as a “could’ve been” is better than knowing “absolutely not.”

No matter what, that was 32 years ago and I still hate the fact I didn’t at least try.