Eight Lessons, One Night

I’ve been watching the latest Love Is Blind, like a lot of people, and would you believe I had déjà vu with Ashley and Tyler’s drama?! *SPOILERS AHEAD* This is one of the couples we all are rooting for, but Tyler had kept a secret. Classic Hollywood theatrics. Honestly, I think it’s the withholding of the secret, not the secret itself, that Ashley was upset about. But for those of you who haven’t seen it, Ashley finds out only a week before their wedding that Tyler is a sperm donor to three kids. As I was watching this episode, I had an immediate flashback to one of my first dates and was then reminded of just how crazy this dating story actually is.

But I’m getting ahead of myself. We need to start when The Waiter and I first met. 


The Meeting

I was out to dinner with a friend and The Waiter was… well, our waiter (I was really creative with his name). He was so smooth in slipping his number to me while my friend was in the bathroom that I was caught off guard. To say the least, I was impressed, so I gave him a chance.

The First Date

It was during our first date that he let me know that he was a sperm donor. Contrary to how Tyler approached this subject, The Waiter was upfront about things and, since he was involved in the kids’ lives, he showed pictures and shared stories. I genuinely found it admirable. And surprisingly, given this subject, the awkwardness that you expect from a first date wasn’t there. The conversation was easy and the chemistry was just right!

I’d like to say that our dates only went up from there, but the first date was the peak of what would turn into a big downfall and one very weird night. But we’ll get to that one soon.

The Ending Part 1

After a handful of dates, he ended things with me because I was further along in my career than him. I found this utterly ridiculous since I had only encouraged him, but you can’t encourage someone out of their insecurities! However, he wanted to remain friends and even take me as a date to several weddings he had later that year. Lucky me (sarcasm intended). I reminded him that we were never really friends… but we could try.

That was my mistake. I should have listened to my gut. But I didn’t and then that very weird evening happened… Let’s dig into it.

The Evening in Question

My friend texted me in a flurry saying she’s running late but to have wine ready! Thankfully, I had a bottle of Snoops’ wine (aka. 21 Crimes) at the ready. The irony about drinking this bottle is we were going out to a wine tasting. That was error number one of the night!

We caught a quick Uber to the wine tasting to which we were 30 minutes late… and already tipsy. The night soon turned into a bit of a blur after a couple more glasses of wine and conversations with the local natural wine hipsters. The next thing I remember is us making the bold decision to walk over 2.5 km to get food! Not long, but long for some drunk ladies.

After much complaining about the long walk by my friend, she brings up The Waiter. She wanted to invite him to join us, mainly to prove what he was missing out on. I looked cute and in my drunk and not so wise mind, I thought, why not? She grabbed my phone and texted him. Error number two of the night!

The Waiter shows up at the restaurant with a grin, snuggling up beside me in the booth. Our third error of the night came in the form of us agreeing to go to a local club to meet his friends. The details I could go into on how unhinged some of the things we saw would take too much space on this blog, so for now, I’ll give you the abridged version!

Right after entering the club, my friend starts asking who I think is attractive. The minute I say, “Yeah, he’s cute.” She’d run up to them and ask three questions:

  • “How old are you?”

  • “Do you have a job?”

  • “Are you single?”

If they were age-appropriate and answered yes to the last two, she would say, “Have you met my friend?” Thus unfolded a night of club speed-dating. What I didn’t know was happening while I was chatting up men, was my friend kept saying to The Waiter, “I’ll do this all night until you do something!”

Error number four of the night and to my credit, I would have shot this down had I known about it. Nothing like a jealous man and his ego to confuse the evening.

After getting a couple of numbers from my very own club speed-dating (stories to come later), The Waiter decided it was time for us all to leave. He had my coat and we were being escorted (aka led strongly) to his car. His housemate, who joined us later in the evening, and my friend were drunk, while I was starting to sober up and question some decisions being made.

As we drove towards my apartment, my friend had another bright idea. She shouts out, “You should all come up to Kaila’s! No objections!”

Error number five of the night.

The Waiter parks the car and everyone piles into my studio apartment. I made some tea for everyone trying to sober people up and then opened the balcony door to let in some fresh air. The Waiter followed me out onto the balcony to talk to me. In the corner of my eye, I see my friend slowly close the door. Then she slowly closes the blinds to the balcony. I imagine she thought, “My master plan is working,” as she folded her hands together like Dr. Evil from Austin Powers.

It’s now 2 am and the city feels quiet for a Saturday night. I remember feeling like The Waiter was talking around a subject he wanted to discuss but never quite getting to the point. As I looked out on the city skyline view, I finally said to him, “What do you want?”

Well, he chose at that moment that he wanted to be with me and said something convincing, which I can’t remember. I naively believed him and that became error number six of the night.

We started making out until we heard a crash from inside. His housemate had smashed one of my very nice wine glasses. The Waiter decided it was time to go, but my friend had another bright idea and said, “You should come back. After taking everyone home, you should come back to Kaila’s.” I nodded reluctantly. Error number seven of the night.

He returned with microwaveable popcorn. Not sure why, but before I could put it in the microwave, we were making out again. Like I said, chemistry wasn’t an issue.

My not-fully-sober mind felt like I could be honest with him. I opened up to him about some of my history and that I wasn’t ready for sex that very night.

In hindsight, I think he was absolutely expecting sex and wasn’t happy, but asked to stay the night because it was late. Again, in my not-fully-sober mind, I agreed. Error number eight of the night.

We talked, fooled around, and cuddled. That was it!

The Ending Part 2

Morning came and he left quickly… didn’t even accept the coffee I offered. Before he left, I tried to confirm our plans for the next day. He fumbled over his words about checking his schedule and swiftly left. I knew then and there that he was not a man of his word, and saying he wanted to be with me was just an attempt to get me into bed.

The next day, he cancelled which didn’t surprise me, but we set a time to meet for coffee the following day. After an hour of drinking coffee and chatting, we both had to head back to work.

He had yet to bring up the topic of us, so I said, “You know the other night on the balcony when you said you wanted to give this another shot? Did you mean it?” He looked away and said, “You know I was meaning to talk to you about that. I don’t think so.” I called him out on the fact that if I hadn’t brought it up, he wouldn’t have said anything.

My assumption is he was going to do the slow fade, you know like the Homer Simpson GIF where he slowly disappears into the brush? Well, The Waiter, of course, denied his avoidance but the truth sat in the air like the London fog—thick and vivid. He left and that was that.

The Truth Revealed

I found out later that his very drunk housemate had disclosed a lot of information to my friend while The Waiter and I were on the balcony. Like how he had only broken up with his long-term girlfriend a short bit ago and was looking at getting back together with her. That he was just using me to make her jealous (ie. posting about me on his social media, even on the day he ended things with me— #coffeewithfriends). 

Lots of lessons were learned that night, and as a straight-A student, I have not made those same errors again! I’m all the wiser. Thank God!



Editor’s Note: My friend calls this night her Roman Empire. There are so many things not mentioned that replay like nails on a chalkboard. All in all, I had to talk her down multiple times from wanting to kick his ass. People say I’m too nice… and maybe they’re right.

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