The Woes And Wonders Of Online Pandemic Dating


Written by the dating damsel in distress

I feel like I’m having my Carrie Bradshaw moment. Sitting at my desk, pounding on the keyboard, typing away as the words come so quickly. Some pondering and looking out the window, but mostly I can’t type fast enough to share the hilariousness that has been the last year of dating. But I am not like Carrie Bradshaw. I don’t have trendy, designer clothes hanging in my closet. I don’t live in New York and drink cosmos every night with my best friends. I’m not choosing between two grown men who are fairly established. Nope. I’m a 30-year-old swiping left and right on every dating app that exists, sifting through the weirdos and the creeps. Online dating has never been like episodes of Sex in the City. But maybe it’s better to have my dating life be more comical than dramatic? At least it’s not a horror movie, right? Hope I didn’t just jinx myself.

I used to travel a lot for work, so while online dating has never been successful for me, it wasn’t until 2020 that I actually had more time to really make the effort. Back in the normal days, I would match with a guy and we’d talk for a bit, but by the time he asked me out I was leaving for my next work trip. And by the time I got back, he was on to the next match. I had a few dates here and there, and honestly, those were pretty comical too. One guy was addicted to Altoids, another wanted to split the check for the two beers we had (total — not each). One had never heard of hummus and didn’t know that Mediterranean food was a type of food. And there was one who lived in the suburbs but never wanted to come into the city, so the only way we’d see each other is if I drove to him.

During the past year with dating during quarantine, the guys have been on a whole other level. Maybe I would have matched with these boys sooner had I not always been traveling, but it felt like there were so many fish in the sea as I swiped left and right while we couldn’t leave our homes. Well, as it turns out, I have to keep fishing. The last year has been a comical, pee your pants, can’t make this shit up kinda story. Some borderline this could be in a movie scenes. Some oh my gosh is this real life moments. And some how do guys act like this in their late twenties and early thirties… The hot ones who ended up being weirdos. The nice ones who still ended up ghosting. The quiet ones who just couldn’t take initiative. I’d like to say I’ll look back on all of this in a year or two, laughing about these stories, but honestly, at this point, I just pray I don’t have any more to write. For now, gear up for the stories that have been my dating life. 2020 — you were quite the ride.

Honorable Mentions

The All-American freak

Stanford grad, entrepreneur, active/outdoorsy pictures on his profile all made me immediately swipe right. I was shocked when we matched, and even more shocked when he asked for my number quickly. But as soon as he texted me, he asked about having a threesome with his friend (it was already set up; they just needed a girl). And when I told him that wasn’t my style, he said “I thought so, you looked vanilla. I’m out of your league because I like exotic experiences, but if you’re interested, I have a friend who might be more your type.” He then sent me a picture of his friend (different from the threesome one) who you could tell was nerdy and quiet and probably didn’t have a lot of experience. I didn’t respond.

The boy next door

I matched with him on a Sunday morning and we were having a fun and light conversation. When we realized we lived around the corner from each other, he suggested we hang out later and go for a walk. He told me he was just looking for a friends with benefits situation and I thought I’d give it a chance. We went for a walk and then got a beer, and although I could tell he was very quiet, I thought he was enjoying himself. He texted me later asking if I thought we were compatible. Apparently I was too vicious for his very calm personality, and he couldn’t even handle a friends with benefits type situation with me. Well, at least he was honest.

The dude in need of a chauffeur

Once this guy found out I had a car, he thought he hit the jackpot. He didn’t want to go out, or even get to know me. He only wanted to hang out at my place and only if I drove him there and back. Or if I wasn’t willing to drive, he asked that I split his Uber charges with him. He told me it wasn’t about the money, it was about the “principle”. The majority of us texting was arguing back and forth of why I wasn’t going to drive to pick him up and why I wasn’t going to pay for an Uber for him. Are other females willing to do this?

The untidy guy

We planned to meet up and watch a movie at his place, so like we arranged, I texted him my ETA when I started walking. When I got to his building five minutes later than the time we set, he came down to meet me and was in workout clothes. He said he didn’t expect me to be on time and hadn’t showered yet from his workout. Should’ve known then it wasn’t going to go well. We got to his apartment and he offered me a drink and then went to shower. As I looked around his place, I couldn’t believe he didn’t tidy up. It wasn’t that it wasn’t clean, but it definitely looked like he wasn’t expecting company — especially a girl. Empty Amazon boxes throughout the room, his coats draped all over the couch, his kitchen had nothing put away from making breakfast. And here I was, waiting for him to finish showering. The icing on the cake: He turned music on like it was going to be a nice long relaxing spa shower. I also noticed he had a big bottle of lotion next to his bed. After the second drink, I excused myself. And when I got home, I took a long, hot shower (no music though).

In Order Of Appearance…

The no move man

A nice midwestern man with a good job and a good head on his shoulders. In text, he was so engaging and genuinely interested in getting to know me. In person, we had good conversation, but the spark wasn’t there. We had dinner dates and a movie date and a walk in the snow along the river date (pre-COVID times, but it was still 2020, so it made this list). So many cute, romantic moments, yet he never reached for my hand. Never brushed up against me or “accidentally” touched my knee under the table. And the date I knew it wasn’t meant to be? On our walk, when we walked past Whole Foods and he said he didn’t understand the hype of that grocery store and thought the freshly ground peanut butter they had was disgusting. Little did he know, Whole Foods is my go-to grocery store and that peanut butter is always on my grocery list. Might even be my favorite part of the store!

The horrible texter, the classic ghoster

The first boy I had a FaceTime date with during the peak of shelter in place. We talked for hours and conversation flowed so well. We had similar interests and some commonalities, but I was most attracted to him because he made me laugh. I liked him yet didn’t think we’d have a serious relationship, but what did I have to lose? He clearly wasn’t interested in being serious either — or maybe just not interested in me — because he would wait hours or days to text back and wasn’t the type of texter who kept the conversation going. He ended up ditching me on the second date because he got tied up painting his friend’s apartment. He was honest about it being a friend who was a girl, but spending 10 hours painting someone’s apartment instead of keeping a date was odd to me. Why even plan for both those activities in one day? We’d see each other every 2-3 weeks, and after a couple months, we were trying to make plans for the following week when he just stopped responding to texts. The classic ghoster.

The model with a foot fetish

This guy impressed me from the start by taking such initiative — suggesting restaurants and making reservations. We talked for a couple weeks before our first date, and even though we got along, I was so nervous to meet him in person because I kept thinking: what’s the catch?! In his pictures, he looked like a model! I quickly learned the “pink flags” (not red flags that make me run, but pink flags that make me cautious). He seemed overly obsessed with working out and his idol was a bodybuilder. I wasn’t sure if he was completely listening to me when I talked. And then when he grabbed my foot and told me he loved that I had high arches, I panicked! No one realizes I have high arches except for the sales associate when I’m buying shoes. Turns out he had a foot fetish, and to his credit, he was completely upfront and honest about it. Although I was cautious, I wanted to give him a chance even when he expressed disappointment after I got pink polish during my pedicure (he likes darker colors) or when he repeatedly asked for pictures of my feet. Funny thing is, he ended up ghosting ME! He must’ve found better feet…

The guy who lived in a van

Conversation was so easy with this one. He was a talker, and I liked it. It was fun to feel wanted and appreciated, but I was a little wary of how much he called and FaceTimed before meeting in person. When we matched, he was in Indiana working on his camper van. This idea did not thrill me because while I love to be outside and hike, I am not a camper and I’m not as adventurous as a guy with a camper van would be. Then I found out that he didn’t have an apartment in Chicago and was just planning to live in his van in his work parking lot. Don’t ask how he showered. Long story short, it fizzled out when he went on a road trip. But not before he called me average as he was working out “what made me special”. No hard feelings on my end, but he’ll always be the guy who lived in a van and called me average.

The ballsy gentleman

We had good text conversations but I was unsure if I felt attracted to him. I’m an event planner for a living, so I love when someone else makes the plan in my personal life; one of the most attractive things to me is when a man makes the plan! And I wasn’t sure this guy could grab the bull by the horn. After lots of back and forth, we decided to meet for dinner, but I was already annoyed when he didn’t have any opinion about which restaurant or even what type of food. But annoyances aside, I picked a restaurant and made a reservation. The date was better than I expected — fun and easy conversation — but I wasn’t sure I felt anything more than just friends. He was a gentleman and I enjoyed his company, so after dinner I invited him to my place to keep up the conversation. He didn’t make a move until he was leaving, and while we kissed a little bit, I still wasn’t feeling any spark. He texted me when he got home to say he had a nice time, which was thoughtful. Even though I didn’t feel the spark, he was a nice guy, so I wasn’t going to write him off after one date… Until the next morning, when he texted me asking why I didn’t give him a blowjob. He couldn’t make a reservation, but he was willing to ask that after one date and a make out session?

The fake name bro

I matched with Dean one afternoon and his opening line was “I’m in love.” I wrote back “I’m waiting for the other part of this pickup line.” While it was clear he had been out day drinking, we had some fun banter. There was a little bit of back and forth, and he made it clear he was looking for one thing only. Side note: I actually respect this. If a guy straight out says I just want to see you once, it’s in the girl’s court to say yes or no. At least he was not pretending to want something more to make me see him that night. But alas, I didn’t think about him again until two weeks later when I saw the same pictures on a Tinder profile with the name Jeff. I thought it would be funny to see if I could call Dean/Jeff out for fake names so I swiped right. The next morning I had two notifications: You have a new match and Jeff sent you a message. But when I opened the app, they were gone. “Jeff” probably didn’t remember me at first and then realized, “I’ve already talked to this girl before.” To call him out, I texted him: “Oh hey there, is this Jeff!?” No response, just as I assumed, but I laughed knowing he knew that I caught him in the lie. Wish I had also asked if he lied about his dog’s name too. Fast forward to almost three months later when I got a text from this number saying, “Oh hey there.” I played dumb, pretending I didn’t know who it was, and he said, “It’s Jeff.” I texted, “You mean Jeff/Dean? What is your real name?” He said it was Jeff but at work he went by Dean. That’s a first. In telling one of my friends this story, he decided to take matters into his own hands. He searched Jeff/Dean’s phone number online and paid for a report to see the name tied to the number. Turns out, this guy’s name isn’t Jeff or Dean. This guy didn’t just lie about his name once, but twice. Best 95 cents ever.

The almost one

This guy was the most unexpected surprise of feelings that didn’t end well. I’m not the type of girl who gets swept off her feet or thinks every guy she meets she’ll date or marry. Given the past year’s stories, I wasn’t even looking for the one, not feeling hopeful about meeting a decent guy online who I could have a serious relationship with. But I was excited when I matched with this one because he was attractive — so my type — but wasn’t expecting anything more than casual dating. But that all changed when I met him in person. We texted for about a month before setting a date, and when we finally met in person, I felt completely comfortable with him the minute I saw him. It felt like I had known him forever. His presence put me at ease. Through our date, it felt like he checked every box I have for the one I want to be with. We shared interests, beliefs, and values. We couldn’t keep our hands off of each other, stealing little kisses while watching TV. He wrapped me up in his arms and I felt so protected and safe. He made me feel alive and giddy, and it just felt so natural and right. We ordered food, we watched movies, and we talked and talked and talked. I told him intimate details of my life that I never share, and the way he reacted was exactly how I imagined my person would react. He told me about his mental breakdown that caused him to quit his job earlier in the year and even teared up reflecting on his past. The time went by so fast and we stayed up until 3 a.m. talking as the conversation kept flowing. He told me he felt so comfortable with me at my place, like he was at home. He told me I was such a sweet girl. He told me he loved that I had such a strong faith in God. Like me, I don’t think he was expecting to open up or have the date feel more than a casual get to know you. And I’ll never know why it went wrong in his eyes, or when it changed for him, or if he even felt a smidge of what I felt. But after that amazing 12+ hour date, poof, he was gone. I texted him hi a couple times with no response. And then a month later, I wrote him a long message to tell him I was hurt by the ghosting and all I’d ask is the respect to let me know he wasn’t interested. And when that heartfelt and vulnerable text didn’t get a response back, I knew I had to move on. The non-answer was an answer.

The what if’s and what could have been’s swirl around in my mind. But the hardest part for me to get over is that my gut was wrong, and all my life, my gut has been right. I never had this feeling with a guy where I thought he was it; I never had this moment of seeing a real future with this person. Yet I had all the feelings with him; I felt the spark in my heart and in my head. But for now, I have to remain grateful, and I thank the almost one for giving me a little snapshot of what I deserve. I deserve those butterflies in my stomach when I guy smiles at me. I deserve hugs by a guy who makes me feel protected and safe. I deserve a guy who makes me feel alive, and who I make feel the same. And I know I deserve a guy who isn’t afraid to tell me how he’s feeling — for better or worse.

While my parents did have an adorable “how we met” story, I’ve never had the fairytale idea of love. For my parents, they locked eyes on the road during my mom’s first commute to her new job in a new city. My mom thought he was trailing her when he followed her the entire drive and pulled into the same parking lot, but turns out, he worked there too. He asked about the new girl and the rest was history. Adorable story, right? Have I locked eyes with a stranger during my commute? Of course. But it’s gone no further than that. Ever. As much as I’d love the cute guy on the train to just say hi, or to accidentally bump into an attractive guy in a grocery store aisle, or to have a handsome stranger strike up a conversation on a long plane ride, I’m not expecting that. There won’t be a meet cute. There won’t be fireworks when I meet someone’s gaze. There won’t be this everyone around us freezes and all we can see is each other moment. At this point, all I want is a normal, kind man to swipe right on me. Someone who listens to me, respects me, shares my hopes and dreams, and calms my worries and fears. So, 2021, the bar is low but my expectations are high. And please, no more stories that prompt me to write another blog.