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Dating Success Story: My Favorite Bad Date

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Does your dating success story have a happy ending? Why not share it with our readers!.

My dating success story begins on what seemed to be a very promising Friday morning. After spending the day at work, I had a date planned that evening with one of my sister’s friends whom I had always found the most charming, lovely, and interesting person during our brief encounters.

That she rarely paid me any attention when out with my sister and I, and the fact that she had only agreed to go out with me after her on and off boyfriend of three, then six, and (apparently just to disrupt the pattern) eight months broke it off with her for – supposedly the last time – was not interpreted as a red flag, but rather as proof of her alluring and mysterious persona.

Even my sister’s warnings about her friend’s high maintenance attitude and poor treatment of the men she dated couldn’t dull my sense of excitement and optimism towards what was going to be the dating success story to end all dating success stories.

The Dating Success Story To End All Dating Success Stories…

I began that morning like most others during the week, by getting coffee at the bagel shop located across the street from the office. Alex, my friendly morning barista, was once again tending the counter and we began our usual morning conversation.

Alex has the type of personality that can make even the most sleep deprived, hungover, and grumpy individual (my morning disposition on one too many occasions) feel better about the day, and talking to her was always a bright spot.

The conversations between Alex and I usually ran the gambit from movies, to books, to even the occasional dating success story. Alex had recently mentioned meeting a guy she was trying to get up the nerve to ask out, so I was eager to tell her about my dinner plans for the evening. The shop was a little busier than usual that morning so we only had a few minutes to talk.

I quickly mentioned my date that evening, and told Alex I would let her know how it went on Monday. Perhaps it was because I was so focused on that evening, but it didn’t dawn on me till much later that Alex’s usually permanent and brilliant smile broke ever so briefly after I told her about my date.  I couldn’t be concerned with that, however, as tonight was the first of what was to be many nights my soulmate and I would spend together.

I showed up 10 minutes early…

What seemed like an agonizingly long day finally came to an end, and the time to meet my date at the restaurant she suggested had finally arrived. I showed up ten minutes early with a plan of getting a drink at the bar to help calm my nerves while I waited for my date.

One drink turned into two as my date was fashionably late to arrive, but I had struck up a conversation with the bartender who seemed pleased to have someone to talk to on what was a slow Friday night dinner rush. As my date walked in, I excused myself from the bar and walked with her to a table.

As we sat down, I couldn’t help but notice her stealing looks toward the bar. When I asked her if she wanted to sit there instead, she dead-panned disinterest and our date was officially underway.

To say things started out slowly would be an understatement…

To say that things started out slowly from how in my mind our date was scripted, would make for quite the understatement. My date starred at the menu with a level of concentration generally reserved for determined medical students trying to memorize each of 206 bones found in the human body in alphabetically order.

When our waitress stopped by the table to get our drink order, my date requested the bartender pick out something for her. I thought this a strange request since my date didn’t specify what type of drink (wine, beer, cocktail, etc.) she wanted.

But having already talked to the bartender briefly, I decided he seemed more than capable at his job. Besides, the guy hadn’t taken his eyes off our table since we had sat down, so I assumed he must have been sizing up what our deepest, darkest, drinking desires were at that point anyway.

After the drinks arrived…

After our drinks arrived, the conversation began to flow a little more smoothly, but I couldn’t shake the feeling that my date was only half listening to anything I said.

My date has many friends, and several of them felt the need to call her during our dinner together. On three occasions she excused herself from the table to talk on the phone while standing at the end of the bar.

It was on the third time she was away from the table when I received a text from my sister asking how the date was going and where we were eating. I mentioned the name of the restaurant, and, determined not to let go of my enthusiasm for the evening, I told her things were going fantastically.

The bartender at our restaurant was my date’s ex-boyfriend…

My sister texted back asking if someone who fit the exact description of our very attentive bartender, who at that very moments was starring intently at my date’s back as she chatted away on the phone, was working at the restaurant that evening?

What I am sure seems obvious to you came as quite the surprise to me, when after a few back and forth texts, my sister informed me that the bartender was the same ex-boyfriend my date has just previously broken up with for the fourth time.

My supposed dating success story quickly took a turn for the worse…

As my dreams our happy life together began to quickly crumble like game of drunken Jenga, I threw enough money on the table to cover our bill and walked out. I stopped to consider saying goodbye to my date, but noticed her and the bartender had finally engaged each other in conversation and didn’t feel like interrupting.

As I walked to my car, I called my sister to inform her of the disastrous outcome to my evening. In an effort to raise my spirits, she invited me to a birthday party she was heading to for a mutual acquaintance. Determined to drink away my sorrows, I agreed to meet her at the address she gave me.

I found a nice corner…

Not in a very talkative mood, I found a nice corner I could stand in at the party that allowed me to still seem engaged with what was happening in the room, but removed from actually talking to anyone. After about 30 minutes of feigning interest at a shelf full of various knickknacks our host had put on display, I heard a voice that immediately jarred me out of my stupor.

To my surprise…

To my surprise, Alex (my friendly morning barista) had arrived and was talking to my sister across the room. I immediately went over to say hello, and we began to talk about how stupid I was for convincing myself of how perfect my date was supposed to have been.

As the night stretched on, Alex and I continued to connect with one another and eventually we excused ourselves from the party to grab a drink at a nearby bar. The evening ended with me asking Alex out for dinner sometime, and she graciously accepting my offer.

I must admit to being somewhat dense, as it was only after she and I had been dating for a few weeks that Alex finally told me that I was the guy she had wanted to ask out and that she was a little hurt that morning when had I told her about my date.

It also turns out that Alex had previously declined to attend the party we later met at, but had changed her mind when she decided she could use a little cheering up.

Alex and I have been dating for little over a year now, and she is without a doubt the most fantastic woman I have ever met. My dating success story advice to you dear reader is this: don’t ignore the read flags when it comes to the people you want to date, and always be on the lookout for those people who already brighten your day.

Timothy Lemke is a freelance writer living Portland, Oregon who regularly contributes to the blog of Dr. Nathan Boyle, a dentist in Sherwood.

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