I’ve never been someone who’s attracted to simpletons. I love the dramatic. My favorite movies are tragedies. It should be no surprise then that I pursue the same principles in romance. This here is the story of how I dated a woman for five weeks who broke up with me no less than four times – and I stayed through it all.
Most might assume I have no self-esteem if I’m willing to stay with someone who keeps breaking up with me, but you could also say it’s a sign of someone who doesn’t really care. Sara and I have long heralded the motto of “Do it for the story,” and well, look, I got a story.
“Sheila” and I met on Bumble. If this had been Plenty of Fish or OkCupid, I might have been able to predict the craziness. Instead, we exchanged numbers our first night and never stopped texting.
Our first date went great. We played laser tag, grabbed drinks, played another round, and ended at a bar. We made small talk that hadn’t been covered in our week of texts. We touched on a couple of #serious topics like kids and religion.
We continued texting after the first date. We made plans for the following Saturday and got together at a beer festival. Dedicated readers know I don’t like beer. I somehow managed to down four stouts before Sheila and I were properly drunk. Somewhere between the third and fourth, we started to publicly make out. I asked if we could move to an alleyway because I detest PDA. A cop soon approached us and asked if we could leave because “this is a family-friendly event.”
I’ve never been more drunkenly proud and also soberly mortified in my life. I also don’t know what type of beer festival would advertise that it’s a family friendly event. It’s not like we were spooning.
The following evening, we grabbed dinner and brought it back to her place. This was arguably our third date. Sheila knew I was graduating soon and asked what I intended to do for jobs.
“Actually, I should tell you, I’m moving in March,” I said. I tried to shrug it off. And we did…for a little bit.
Our First Breakup
The next morning, we exchanged a few pleasantries by text. Then, an hour later, I received my first breakup text:
“Hey, Cazey, this may be too soon to say this, but I don’t want to mislead you. I think you’re great, brilliant, funny, handsome, etc., and I enjoy hanging out with you. However, I don’t see this progressing romantically.”
The text was the longest paragraph in our history of texts. This may be overstating a bit because I tend to send paragraphs of information in haiku-form, but this was an unbroken text block. It felt slightly heavy-handed given three dates. If I’m all these things, why don’t you see it progressing, Sheila? Why do you think I want it to progress, Sheila? Hmm?
After 15 minutes’ pondering, I replied, “I appreciate you being upfront. I’m not looking for anything in particular, so we can keep hanging out as friends.”
Don’t roll your eyes at me. I am not someone who likes to maintain friendships with exes, but this was a weird period in my life, and I was actually down for an experiment. For a host of reasons that I won’t divulge here, I wanted to see if I could have a friendship with someone I’d been with romantically. (Another blogpost to come!)
“You’re much cooler about this than most guys are,” Sheila commended my response.
Well, I’m not most guys, I thought. What I really should have been thinking is, How many guys have you done this to?
Surprisingly, we continued texting. Relationships came up. Her past one and my brief fling the previous year, specifically. She asked if my last five years of singlehood had been intentional or just happened that way. I am not embarrassed by my singlehood. At all. Actually, get me a soapbox. But it is a hard thing to explain to someone I’ve just met.
This led to some exposition on what I am and not looking for (undecided mostly). Sheila said this surprised her since I brought up kids and my job in the first three dates. Whelp. I’d been misread, not entirely without reason.
We agreed we should keep flirting. We had already planned a date for the following day before the first breakup. I gave Sheila the option to reschedule, but she insisted we still meet for ice cream. Ice cream became rooftop drinks. Afterward, she invited me back to her place.
Me: “Are you sure?”
Following this fourth date, we continued our hourly communications. I went away on a short trip abroad. The weekend I returned, I had been invited to gala and had an extra ticket for a date. Naturally, I invited Sheila.
“Can I have some time to think on it?” she replied.
“Well, sure,” I said.
Our Second Breakup
Sheila is the sort of person who always asked about me. She expressed constant interest in how my morning was, how my day was going, what was I doing right now. I’m not used to such chatter, but it does feel nice when someone cares. We continued down this path of conversation until, several hours in, Sheila announced, “I would like to go to the gala with you, but I’ve decided we are better off as friends. If you want to bring someone else as your date, then you can and I won’t be upset.”
Before I invited Sheila, I had worried the gala invitation sounded very couple-y. And it seemed she may have been thinking the same thing.
I replied, “I’m not talking to anyone else, so I’ll be bringing a friend either way, so you’re welcome to come.”
“I’d love to come,” she replied.
We ended the conversation on a neutral note. She would come to the gala. I had no expectations beyond friendship.
The next day, Sheila texted first: “Good morning. How’s your day going?”
Sheila drove herself to my apartment before the gala where we met up with some other friends. I told my friends beforehand that we were just friends. Of course, a friend’s date then asked us, “How did you two meet?”
We both stuttered.
“Bumble,” Sheila finally responded.
“It’s always great when it doesn’t work out and you two can just be friends,” the person said.
We’ll see if that’s true, I thought.
An hour into the gala, Sheila seemed especially flirtatious. We kept bumping into each other. She rested her head on my shoulder. We decided we both needed to use the restroom. The hallway outside the restroom was empty. It was still empty when we came out of our respective bathrooms. She looked at me. I looked at her. She wanted to be kissed. So, we did.
The next morning, we went to breakfast together. We kissed goodbye. She asked if I wanted to meet up for dinner. We got cocktails after. She came over the next night for drinks in my garden. We ended the week at her apartment, ordering in and watching a scary movie. In the morning, she asked if I wanted to grab coffee. We sat outside for over an hour and wandered into local shops.
On our way back to her apartment, she brought up this very blog. “You seem to write a lot about dating,” she said. “Are you going to write about me?”
[Editor’s Note: LOL.]
“You’ll have to wait and see,” I laughed. “Or do something really worth storytelling.”
Our Third Breakup
An hour and a half after I left her, I received the third breakup text: “Hey, Cazey, I know I’m sending mixed signals. I’ve really enjoyed our time together, but I think we’re better off as friends.”
Mixed signals? My broken WiFi router couldn’t send more mixed signals.
Earlier in the week, I had made a bet with my friend that Sheila would break up with me before the weekend. My friend thought not.
I texted Sheila back: “To be honest, I was curious if this would happen again.”
She did not reply. But we continued Snapchatting and sending memes over Instagram.
Two days later, she texted asking how I had been. What was I doing tonight? Did I want to come over? To watch a movie maybe?
This is when the reader and I exchange looks.
“Sure, I can be there in 45 minutes,” I replied. “What will we watch?”
Our Fourth Breakup
We started off on opposite ends of her couch, but that didn’t last long. Soon, between kisses, she said, “I’m sorry I keep being so confusing.”
“Yeah, we should probably talk about that,” I said, also between kisses.
The kisses eventually stopped. We needed to have a serious talk, though I didn’t feel very serious about it. I tried to guide the conversation by asking what we wanted. The thing about asking that is, you need to know what you want, and I didn’t know what I wanted other than momentary entertainment. Which isn’t a reassuring thing for anyone.
She similarly hesitated to voice what she wanted. We both agreed neither of us wanted feelings, though that window seemed to be closing fast. Though I also might have been tending toward feeling numb after three breakups. Was this our fourth?
Yes, it was.
“All I can do is friendship right now,” she concluded 12 hours later by text message.
Isn’t that what we’ve been doing? I almost replied.
Of course, the reader and myself knows better than to discount our fourth breakup as the finale to this saga. The very night after our fourth breakup, Sheila asked what I was doing. In my newfound singlehood (just kidding), I had decided to go to the movies by myself. I answered as such.
“Can I come?” she asked.
We then made plans for a party that weekend. Just as friends, of course. Insert eye roll emoji.
For the first half of the party, I felt excited to be with Sheila, but at a certain juncture I looked at her and thought, “What am I doing?” But how to end something if you aren’t actually together? And, naturally, Sheila had driven herself to my place and was in no state to drive home.
I needed to break up with her, but that would entail we were together. Which we weren’t. In fact, I had gone on dates with two separate people since our third breakup (one of the dates which I scheduled between our second and third breakup; at the time, I questioned if I should go through if I was “with” Sheila).
When we awoke, I immediately made a list of all the errands I needed to accomplish that day. “I have coffee in my fridge,” I said. “I can give you a to go cup.”
Over the next two weeks, we stopped spending so much time together. I pursued someone new, but did not disclose such transgressions (was it even a transgression?). We never kissed again. We slowly sat farther apart on the couch while watching Netflix. And she dropped out of my top Snapchat friends.
I can’t say I ghosted, but I may be able to say this is my final goodbye.