Guy One: The Shy One With a Surprise

I “liked” Guy One’s profile immediately. It was simple, included two photos of himself but mostly included his photography works which included pastel nostalgic edited photos of sunbathers at the beach. His profile was simple but he came off as sincere, so we matched up and started chatting. 


We decided to meet halfway in Los Angeles. We met for tacos, and I immediately came across my first dating dilemma as a recent divorcee brand new to the life of dating apps – who pays for what?! When I was dating “back in the day” the men would pay for everything. This is not to say that I am a freeloader (trust me, I’ve been in relationships where I was practically a sugar momma), but what is the expected norm now? To make matters more confusing, Guy One was 28 years old, I am 32 – yes making me a “cougar” but also I wasn’t sure what these “millennial” young boys expected now.

I decided to make the decision to order first and immediately whip out my wallet as a clear sign that I would being paying for myself. My rationale being that if you are on a dating app, you are most likely going on a lot of first dates and it can get expensive after a while. Later on a girlfriend will tell me she does NOT respect a guy who won’t pay for her, or at least offer to pay because her time is valuable and he should be able to dish out at least $15! I’m still not sure how I feel about this. I think on a first date it would be nice if they offer to buy you a drink, but they are not expected to pay for the entire outing unless they can afford it.

Anyways, guy one was a very handsome redhead with dark shark eyes. I know that sounds scary but to me it was quite gorgeous and intriguing. However when he opened his mouth he released a very high and squeaky voice – which was confusing since I did not expect it based on his looks, but something I was able to deal with.

However throughout the date I realized he had some insecurities. He was VERY shy and would not always make eye contact with me. I felt as if I was talking the entire time through our date. He would shine only when I would purposefully ask him about something I knew he was an expert in. 

After we finished our tacos, we walked around the neighborhood and ended up at a bar down the street. That’s when I remembered, he DIDN’T DRINK. I knew this ahead of time but didn’t realize how awkward things would feel as he sipped on some water and I was on my second whiskey drink. It felt like a job interview. Yet still, I managed to keep the conversation going while he sat there and smiled at me. When it was time to go he told me he had a really good time and asked if I wanted to do it again. This having been my first date ever since my divorce I agreed because…well he wasn’t a serial killer and even though we did not click, I decided to give it another shot – it would at least be good dating practice. I was also just very happy that someone thought I was dateable. 


Our second date was in Pasadena. Again, he was very shy and quiet.  He looked like he was wearing the same outfit he wore to our first date – black Patagonia rain coat and jeans. The date went as the first one did, me talking while he smiled and stared at me. I tried to make it more interesting by planting the idea of going to an arcade. He was kind of nerdy so I thought he would appreciate this idea. The plan worked! We went to an arcade and ended up having a nice time playing retro games. At the end of the night I told him I needed to go home and he offered to drive me home. When we got to my house I turned to him to tell him I had a good time and paused for a few seconds to give him the opportunity to lean in for a kiss. The three seconds came and went and I just gave him a hug and went home. 

While I was crawling into bed in my PJs that same night, I got a call from Guy One. Thinking it must have been an emergency because….who calls someone now instead of texting…I picked up. He went on to tell me he had a nice time and asked me if I did too. “Yes, I did” I responded. Which he then replied with “I don’t know how to say this…..” immediately I thought he was going to tell me he didn’t want to see me again and just didn’t know how to end the date. Instead he finished the sentence with “I’ve never been affectionate with another female.” Which I translated for him as, he’s never done anything sexual with a woman. In big relief that he wasn’t disappointed with ME, I said “AWWWWW that’s so cute. Thank you for telling me” which in retrospect was probably humiliating for him.

I then told him we could just be friends and he told me “NO, I don’t want to just be friends.” I then made the joke that I could rape him one day. Again, very very dumb joke I know this. He awkwardly laughed and we decided we would go on another date.

Fast forward to the next day and I’m talking to my girlfriend who convinced me that the last thing I need after getting out of a marriage is to date a virgin who would need to be taught everything. To be honest, I didn’t care he was a virgin, the biggest thing for me was that we didn’t click and it was quite honestly exhausting to go on dates with him. If I couldn’t even enjoy a date with him, why would I go through the trouble of helping him lose his virginity. I am a people pleaser and a I needed someone who would be a natural match.  I called him later that night and told him I didn’t think we would see eachother again as I was not romantically interested in him. His response was “aww that’s a bummer.” I felt horrible, but it was probably for the best. I just hope he didn’t think I decided to stop talking to him after I found out he was a virgin. 

Leave a Reply

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out /  Change )

Google photo

You are commenting using your Google account. Log Out /  Change )

Twitter picture

You are commenting using your Twitter account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s