Feedback 2021: The Anna Misadventures

Once in a long while, I might receive an email from a reader seeking a sympathetic ear. This one wasn't a horror story or an interpersonal disaster, but I thought it was worthy of a public viewing not only because the author put a lot of work into it but also because it shows the kind of mundane struggle in the quest for human connection that may be easier said than done.

The following story is not only relatable-- similar anecdotes could come from plenty of other people-- but it illustrates how the simple act of taking a woman at her word is not necessarily the forthright act of communication that you might hope for. Somewhere along the line, someone failed to tell this dude the truth about the bare-knuckled reality of pursuing relationships in college and in adult life if you're simply... average.

How much irritation could be avoided if more people simply said: "Guess what, son? When a woman stands you up for a date, saying ‘sorry, but maybe next time’ you should take that to mean there will never be a next time." Even if you were to succeed with such a woman later on, either of you have already failed a very basic test.

I think this speaks to a deeper point which is low and slippery enough to glide under the radar: For whatever reason, people have been failing to mentor large swaths of younger men. And by "people" I mean parents, teachers, older role-models and folks who really ought to know better. They-- we-- have failed to teach young guys about their inherent value, failed to teach them what works and what doesn't work in life, and failed to teach the important lesson of when to cut your losses and look elsewhere.

Stan's Story

I was a total loner for five straight years in college. I saw all of my friends moving in and out of relationships, which seemingly left me as the sole person who never had a girlfriend. One of my only sources of companionship and human interaction was being friends with Jacob, whom I met in one of my classes. Jacob and I had a lot in common with each other- both of us were nerdy, wore glasses, were Asian, quiet, and neighbors on the same dorm floor. When I met him in freshman year, he noticed that I did not have a girlfriend. One day, while both of us were drinking together, he admitted that he had something of a "girlfriend curse." Every one of his friends ended up being in a relationship while he was left out, single and lonely. That’s when he made a bet with me: by the end of sophomore year, if I had not gotten a girlfriend by then, he'd pay me $10. I didn’t know if he was being serious or not, so I just laughed it off and accepted the deal. Sure, why not?

Eventually, I began observing the dating market in my university and how social dynamics work alongside it. A big pretense as to why I couldn’t get a single girl to go out to coffee with me was that every girl that I talked to said they had a boyfriend. Half of the time, that was a blatant lie to preemptively ward-off unwanted attention from guys they deem to be unattractive. Of the thousands of girls that I talked to in my entire five years in university, whether it was in class, the dining hall, clubs, get-togethers or parties… how is it statistically possible that not one of them is single?

Around the time that I was getting interested in dating, I noticed a girl who was in one of my classes. During the first week of class, the TA made us introduce ourselves. I said "Hey, I’m Stan, I’m a second year student, and my major is computer science." After the introductions, the girl who sat in front of me turned around and asked me what computer science classes I was taking. "Wow, a girl who makes the first move", I thought. I was instantly flattered. I told her what I was taking and she was impressed. Her name was Anna, a third year studying art, who used to study computer science before changing majors. In retrospect, I had no clue what made me fall for her, but first impressions can definitely warp people’s perceptions. When she spoke to me, I felt instantly attracted. I didn’t see her as some shallow or ordinary girl who curves the guys she doesn’t find attractive. I saw her as a fellow intellectual who was passionate, driven and who loves science. It would be a massive understatement to say that I was smitten- I was determined to date Anna.

We quickly exchanged numbers and were soon texting and talking every day. There were so many things we had in common. Interests like anime, movies, board games- the list went on. Anna liked practically every hobby that nerds would like and even more. I'd struck a gold mine- I needed to make my move!

I went ahead and decided to ask her out. I sent her a text saying:

"Hey Anna, it's cool to know that you and I have so much in common. How about we talk about Stranger Things or Star Wars while getting coffee? I know a good place just downtown."

Two minutes later, she wrote back.

"I really want to know you too!! But this quarter has been killing me, and I’m super busy. I got finals to focus on, so why don’t we meet when next quarter starts?"

"Huh, you seriously can’t even spare half an hour of your time to meet with someone downtown?" I thought. Then again, maybe she really is that busy. Maybe I need to cut her some slack and be patient with her. I texted back:

"Sure thing, no prob. May the Force be with you 😀"

Fast forward to Christmas and the next quarter had already started. I wanted to make 2016 a year of terrific memories. I was still sweet on Anna, so the first order of business after returning to my campus was texting her to see how she was doing. We scheduled to meet at that same coffee shop in a week’s time and I just couldn’t wait.

On the day we were supposed to meet, I had just finished attending my last classes and I was waiting in the coffee shop for her to arrive. Literally five minutes before our appointed time, I got a text from her:

"Hey Stan, I’m really sorry. Something really urgent came up and I need to cancel our coffee date. Can we reschedule?"

What the...?! She had "something urgent" that came up just a few minutes before we were supposed to meet? Give me a break. But I needed to act chill in the text messages. I shot her a quick text:

"Hey, it happens to the best of us. What day works for you?"

We ended up rescheduling for February 13th. Since our date was planned just before Valentine’s Day, I wanted to make the date as memorable as possible. I went downtown to See’s Candy and bought some chocolates to give as a surprise gift. There’s no way she’d flake on me this time, I thought. She certainly sounded interested in the text message, if that’s possible.

When I woke up the next morning, I got a text from Anna:

"Hey Stan, I’m feeling super sick right now and I’m throwing up everywhere. Can we reschedule to next week?"

What the hell? Again? Around this point, I began to wonder whether or not Anna was just toying with me with all these excuses, but my rose-tinted glasses still warped my decision-making. I sincerely believed, at the time, that she was interested in seeing me but had some sort of anxiety issue when the time actually came. Then I stared down at the chocolates and devoured them myself so they wouldn’t go to waste.

Around that time, I talked to Jacob and brought up the topic of how Anna was flaking on me all the time but still seemed interested in me. He speculated that she really does have anxiety and that‘s the reason she is always a no-show. Then he suggested that maybe we all hang out, as a group gathering, rather than invite her on a one on one coffee date. I don’t know what was going through my head at the time, but I actually thought maybe that it was a good idea to get Anna acquainted in an informal, casual environment. So I texted Anna:

"Hey Anna, my friend wants to grab dinner. Care to join us tomorrow at 7 PM at Pizza My Heart?"

She responded almost immediately with:

"Sure thing, Stan! My schedule is free all day tomorrow lol"

By that time, I was starting to take off the rose-tinted glasses because I had the sinking feeling that she wasn’t going to come. Nonetheless, I gave her the benefit of the doubt since I still believed she might’ve been having anxiety issues. The next day, I gave Anna another text:

"You still on for tonight?"

"Yeah, I promise I will make it this time. I love Pizza My Heart and I really want to have fun with you tonight! 😀"

By 6:30 PM, Jacob and I headed down to the restaurant, got a nice booth and ordered some pizza. 7 PM came and there was still no sign of Anna. I sent her another text:

"You coming?"

She replied with:

"Yeah, I’m going to be a little late sorry 😔. I’ll be there in 15 minutes."

Totally reasonable. Jacob and I sat back, relaxed, made random banter and waited. Before I knew it, an hour already flew by and Anna was nowhere to be seen. I was starting to get angry at how Anna not only wasted my time, but Jacob’s. That’s when I got a text from Anna:

"Stan, I’m so sorry but my group project is due tomorrow and my group isn’t responding. My project is blowing up! I need to cancel our get-together and hang out with you another time."

Whaddaya know? What can you really expect from a flaker, anyway? Although Jacob shrugged-off the whole affair, I was irate that Anna had wasted our time that evening. But that wasn’t even the main kicker. A week later, I got a text from Anna saying:

"Hey Stan, I’m sorry but I think that you might be getting the wrong hint- I’m not interested in anyone right now."

I guess I didn’t know how to react. The minute I read what she had sent, I burst-out in laughter. After more than four months of back and forth flaking, now she tells me she’s not interested? Then why the hell didn’t she say so earlier? Angrily, I sent something along the lines of:

"Why the hell are you telling me this now, and not back in December? Do you even realize how much of my time you’ve wasted going back and forth? How could you be so dishonest with me the whole time?"

Not surprisingly, I didn’t get a response. When I told Jacob about what happened a day later, he told me that he had texted Anna to ask her how she really felt about me. She replied with:

"I think Stan’s a great guy, but I’m just not interested in relationships right now. He can attract a sea of women out there in the world. I never replied back to him because I don’t want any drama, and I never led him on or anything like that."

Thanks for being such a bro, Jacob… wait, what? Are you serious? She never led me on? What the hell is she talking about? All the flaking, pretending to be interested, rescheduling, wasting my time at the last minute- did she really have the audacity to say that she didn’t lead me on? After this display of gaslighting, I blocked Anna’s number and never spoke to her again.

A few months later, Jacob and I went to a dive bar downtown and at some point, we got drunk out of our minds. I don’t remember what led up to Jacob talking about girls and dating, but at some point, he brought up the topic of my misadventures with Anna.

"Hey, aren’t you still single?" Jacob asked.

"Oh yeah."

"Uh huh. Remember last year you told me you’d give me $10 if I can’t find a girlfriend by the end of sophomore year?"

"Yeah I did, haha! Let me Venmo you right now."


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