Dating Your Crush is a Terrible Idea

Okay. Trust me when I say, NEVER GO ON A DATE WITH YOUR CRUSH.

For some really odd reason, people think I have this natural ability to be good at dating. Boy, are they all wrong! I spent the majority of my twenties dating the same guy. It was on and off, but nonetheless, close to a decade of my adult life went to one person. So, I’m an expert on dating my ex, but when it comes to anyone else, I’m a complete novice. He and I have broken up for good this time, so now I’m trying to date and I’ve realized that dating is like, not even hard, it’s impossible. I’ve basically resolved in my mind that unless I am fortunate enough to find myself in an arranged marriage, this may never happen. But for some reason, I’ve remained hopeful and very open to any new potential opportunity. Yes, dating is like a job to me. And the biggest issue isn’t getting a date; it’s getting a quality date. And when you get a QUALITY date, you’d be surprised by the extent I would go to make the date actually happen. And now, it’s story time…

I talk a good game, a really good game—especially when it’s on social media or over text. I take many liberties to push my limits and on one particular day, I was definitely feelin’ myself. So there’s this guy, I’ve had a crush on him for YEARS. He’s a writer, social activist, business owner and musician. Many of our interests overlap, but because of his legit stardom, I just admired him from afar. This dude’s résumé is mad impressive, yo. (Sometimes I forget I’m not from NYC.) I became a fan of his because of his poetry, but he is no starving artist, let me tell you! His business is successful, he has published books, released albums, he’s part of a panel at Harvard, a guest on NPR and Ted Talk… the list just keeps going. He is totally someone who is worth the time and energy if you ever get the chance. Our shared interests included the world of art and writing as well as social activism—he’s just way more successful at it! He and I were friends on Facebook, and suddenly one day, HE STARTED FOLLOWING ME ON INSTAGRAM. You have NO IDEA how juiced I was to have someone of his caliber even take the time to push the button “Follow” for some peon like me (usually I speak extremely highly of myself because, well, I’m amazing… this is just for effect). When I received the notification that he was following me, I dang near passed out. I even made a meme with that cute little seal with the awkward face that said “when one of your poet crushes follows you on IG and you’re trying to play it cool.” I mean, you would have thought Michelle Obama sent me a “wanna grab coffee?” text or something. It was at that level for me! But still, I wasn’t giving it much thought because with the women he has at his disposal, I for sure was nowhere on his radar. I mean—we don’t live in the same city or area, we don’t have mutual friends, we don’t brunch together, there was no visible link to connect us at any time. But like I mentioned, I talk a really good game! I am a writer for a reason. 🙂 One day, he posted a video that was a little on the more… how should I put this… sexy side. He was comparing intimacy to playing an instrument, and me being so bold, I commented something a little flirty (more like naughty, but I like to say flirty!), asking if he gives lessons in his, ummm… instrument of choice. Yeah, I went there. I thought nothing of it after I hit send and truthfully I thought he wasn’t going to respond. But to my surprise, a few weeks later, HE DIRECT MESSAGED ME! I’m not joking, I opened up the IG app on my phone and he was saying something flirty, along the lines of how I don’t really want lessons. I think I had a panic attack while I was reading his response! Normally, I can give a witty comeback (that’s why my nickname is Whitty… not really but I can pretend!), but I was NOT prepared to hear from him. I even told him I was having a fangirl moment (I’m such a dork) but I guess he found it endearing. It wasn’t even 8am on a Saturday morning when I saw this message he sent the night before and I began to call all my sisters! I had to talk to someone! I got ahold of two of them and told them what happened. They were in shock just as much as I was! I had to make this conversation lead to more than just flirting. He’s a Bay Area native just like me, and comes into town often. He told me he’d be in town in a few days and wanted to go out! I was so excited I could not even sit still. While he and I were exchanging messages, I was in a group chat with three of my sisters discussing what was going on, consulting with them on what each response should say, and analyzing everything he said too. See? Dating take a lot of work! It took an entire committee on my end to even make this happen!

So I had five days to get ready for this date. Five precious days to prepare is no time at all when you’re going out with your long-time crush! I was contemplating going on a cleanse so I would look like absolute perfection, I went shopping for a new outfit, I ordered a cute top I might wear, bought a new concealer from MAC, and practiced putting on eyelashes. Two days before the date, I pulled out literally at least thirteen outfits and piled them in the corner of my room just in case the outfit I had decided on ended up being eligible for the worst dressed of 2016. That same night, I was going to dinner with a youth group I volunteer with. I was having a great time, but out of nowhere when we were heading home, I started to feel like crap. I was completely drained and felt nauseous. All I could think was, This cannot be happening, not now. No way. I cannot get sick. I was so afraid, but then it dawned on me: There has been a flu that has been going around my company for almost two months now. We work out of three different offices, but I had gone to one of our other offices and was helping out with some of the work of another coordinator because she was out sick with the flu! AND I SAT AT HER DESK. It was at that moment that I knew I messed up. I tried not to panic, I just knew I had less than two days to get better. I REFUSED to miss my date. This was a real shot at a quality guy and come hell or high water, I was going to be there.

That night, I started my own self-medicating remedies to get better. I basically took every item in my medicine cabinet until I began to feel less sick. I had a terrible night and barely even slept. The next day at work, I felt like death. I should have stayed home, and that became very apparent when I was trying to work while quietly dying. I had taken two different types of vitamins, cold medicine, flu medicine, anti-nausea medicine; I was drinking apple juice and eating only crackers and Jell-O. I didn’t want to eat anything that would make it worse, and did everything I could to flush the flu out of my system. I decided it was time to go home because I had to get better by the next day. That evening, on top of everything else I had taken, I also took two Benadryl to make sure I slept all night to allow my body to get better.

The next morning I was better-ish, but so giddy that my big day was finally here! One of my sisters texted me bright and early telling me how excited she was too. She said she felt like she was going on the date instead of me. I already had made up in my mind I would work half the day, go home, rest then get ready and be at my date at 6pm. So essentially, that is what I did. I pushed through the first half of the day, headed home around noon or 1ish, and jumped right in the bed. I had already taken three different medications and made sure to eat my good old crackers and Jell-O so I was ready! Around 3pm when I was waking from my nap and feeling much, much better, I get a text from him—he suggested us meeting up at 5pm instead. While I was completely aware there was NO WAY IN THE WORLD I could make it by 5pm across the Bay Area during commute hours and I had not even put a single beauty blender to my face or comb to my hair, I agreed to make it there by 5pm. Why? Because I’m clearly delusional and insane.

So I begin my journey to beautification, and I think I literally tried on EVERY single outfit I put out. I had my designated outfit that looked HORRIBLE. So one by one, they piled on my bed when finally I picked a cute black dress—I mean, you can’t go wrong with a little black dress! Even with all my efforts, I was walking out the door at 4:39 PMMMM!!!!!!! I know! What was I thinking? I had done so much to make this happen, and now I was going to be late. Even without traffic, it would have taken easily forty-five minutes, but with traffic it would be much, much longer. So when I hit the road, I quickly texted him to let him know I was running late, and of course his next questions was, “How late?” I told him probably about half an hour. Yeah, no such luck. So about 15 minutes he texts me again asking me if I was close. I apologized (again!) and explained to him the traffic. He told me jokingly, “Clearly u hate my guts [sic]”, and I just wanted to die! I was hurting this guy’s feelings (albeit unintentionally) and I was so upset with myself. And why did he want to know where I was, you ask? Because he had already ordered for me. :-/ Do you know how sexy it is for a man to be decisive enough to know what he wants but also know what I want as well?

Another twelve minutes passed by, he asked if I was close, but of course I was still stuck in traffic. I asked him not to leave, and he’s so freaking sweet, he was like, “I wouldn’t leave you, love. Your food came and I don’t want it to get cold.” WHO ARE YOU?! How did I become so lucky to even be noticed by a man so kind and considerate??? Ridiculous. I told him, “I deserve to eat cold food”, and he’s such a sweetheart, he told me I don’t deserve cold food, when I truly believe in the bottom of my heart, I wanted me to eat that dang cold food for having him wait on me.  He then told me he would just get it boxed up for me and we could go somewhere to get some tea or dessert.

Finally I ARRIVED!!! It took a few minutes to park, but there was space in some random parking lot. I didn’t even care if I’d get a ticket or get my car towed—I was too late to care! How late was I? Oh, just an hour and sixteen minutes. And he looked so freaking adorable with his navy blue blazer and khaki pants and dress shoes. I don’t think my prom date looked that handsome! When I got there, I was super frantic and gathered my thoughts and he was so patient and kind. He paid the bill for our phantom date and we decided to head out. He had flown in and was flying right back so didn’t rent a car because like, who does that anymore? So he offered to call a Lyft but I said that’s crazy, I have my car. So we were walking out the door as I tried to open up my umbrella… did I mention that? Yes, I had this awe-worthy man waiting for me out in the rain. I suck. But he insisted on using his and walking me to the car, making sure I was completely covered. We drove over to a tea spot and I made a complete fool of myself asking what honeybush was, and the tearista (??? is that a thing) made sure to make me feel like a moron by replying, “It’s honeybush.” Thanks. It all makes sense now. Please do not neglect the sarcasm. But once we got settled in, we had a fabulous time. We laughed, we teased each other a bit, they had an old-school PACMAN game we both played, we talked about more serious topics, I got to tell him more about me and my background… I couldn’t have asked for a better conversation. Oh, I forgot to mention! When we were walking in, a homeless guy was sitting outside asking for a cup of coffee which my date of course got for the gentleman. I was so appreciative of this guy and everything he did on our half-date.

I drove him to his friend’s place where he would stay the night. He hugged me and told me to text him when I made it home. Despite the slow start, I thought the date actually went pretty well. I had already decided I would make this up to him when I wasn’t sick any longer. But the opportunity never arose.

When I got home, I texted him saying I made it home but no response. A few days later, I texted again, apologizing and telling him I wanted to make it up to him. We could go on another date when he was in town, do whatever he wanted, go anywhere and it was all on my tab. No response. A few days later, I got a text. He told me, “I too enjoyed being left in the rain, eating alone, conciliation prize of tea with a crazy person [not me, we were close to Berkeley lol] coming in and out then being dropped off on a hill in the dark. It was magical.”

I. Was. Stunned.

I still must have been very high on cold medication, because I had a much different evening than he did. We spoke a little more here and there—I even came to a show he had in the Bay Area—but it just wasn’t getting off the ground.

Him being my long-term crush definitely affected the date overall. I wouldn’t have done half the crazy things I did if he were a guy I just met. If I could do that night over, I first would have gone on a few practice dates the days prior to get me back into the rhythm of dating. I would have made arrangements to come to one of my girlfriends’ houses that was local to the restaurant so I wouldn’t be so late. Also, I just wouldn’t be so late in general. I would have stuck with the 6pm dinner time, and be only 16 minutes late, which is more reasonable. I definitely would have rescheduled if I were still sick and not almost overdose on different medications to make myself feel better. I think if I were my 100% self, the date would have been ten times better at least. I would have also done the “reach,” ya know, when you reach for the check acting like you’ll pay it, and then when he says, “I got it” you say, “Are you sure?” then of course he says “Yes, I’m sure—but I appreciate the offer.” And maybe I would have kissed him on the cheek. Overall, I’d probably give myself a grade of D+ on the date, mostly because of how late I was, that’s unacceptable, especially for a quality man as such. It was an incredible opportunity, on clearly the worst week of my life, and my lack of dating experience really crippled me.

Did I mention he had a pocket square? Ugh.