The Highs And Lows Of Online Dating

Anyone who’s ever tried it knows that online dating can be exhausting. Sometimes it’s great, other times it’s awful. Here’s some of the memories that stood out during my time of online dating. You’ll meet Shakespeare, Hillsong Divided, Indiana Jones, and Casanova, four guys I “met” online and then in person.

First up is Shakespeare, the first guy that I corresponded with for awhile. He wrote me lengthy, beautiful, thoughtful emails about life and faith, he asked great questions…he seemed so perfect for me. Could I really hit it off with the first person I seriously corresponded with? I wondered.

We met for burgers and milkshakes at a diner halfway between our two cities. He was a nice guy, but I think we were both very shy and nervous. Was he enjoying our time together? I couldn’t tell what he was thinking, but the connection just didn’t seem to be there between us. 

He sent me a lovely “I don’t think this would work out between us” email later. I couldn’t understand why we had such a connection through writing, but not in person. It must be a fluke, I thought. Oh, how wrong I was…

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Next, we have Hillsong Divided, the worship leader* who did not. know. what. he. wanted. Or at least, he didn’t know how to say what he did/did not want.

We met up for coffee for our first date. He was very late, but I knew that the city traffic was crazy. We ended up going out for dinner and talking for hours. We went on another date, and he was late again. We went on a third date to a concert and dinner and had a great time.

He said we should hang out on a Friday, then he waited until the day of to make a plan. “We should hang out soon,” he’d say again. But then he never made plans to do so. I waited, then finally called him about why the plan fell through again and he told me he had to drive two hours out to the suburbs and get his phone fixed. There were very mixed signals with him: He’d tell me I was pretty, that he enjoyed spending time with me,  tell me the lines about “hanging out soon,” but then he didn’t make much effort. Looking back, I realize that his lack of effort should have been a red flag, but I didn’t recognize it at the time. I found out that he was talking to another girl and that was that.

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Hillsong Divided. (Not really him.) 

Then there was Indiana Jones. We’ll call him “Indiana Jones” since he was from a city in Indiana. We had many long conversations through Skype, so I thought I had a good sense of who he was. He was funny, kind, confident…it seemed like we would have a great time when he said that he’d visit. Unlike Indiana Jones, his tolerance and comfort level for new and exciting things ended up being drastically different than what I expected.  

He drove to my city to see me for the weekend. While planning his trip, he’d asked several times if he could sleep on my couch because hotels were expensive where I lived. Um, no. (You’re nice, but you are a stranger, Indy.)

After he arrived, we took the public transit into the city and went on an amusement park ride. I was having a good time, snapping touristy photos with my phone, when he asked an odd question:

“So when will your hair grow out?”


“What do you mean?” I asked casually.

“I don’t know… it’s kind of…uneven,” he said.

“It’s supposed to be that way,” I replied. (For reference, google “asymmetrical pixie cut” and you’ll see some similar examples).

I didn’t really care that he didn’t like my hair, I was more annoyed by the fact that he acted like it was something that needed to be fixed. The rest of our time downtown was awkward. 

He went back with me to my apartment, where I found out some of the reasons why he had been acting strangely. Turns out that he wasn’t comfortable taking the public transit and being in close quarters with other people, and felt overwhelmed by being in the city in general. He decided he should go, and he left. We had planned on going to dinner, so I was confused and hurt.  

He called me about 15 minutes later from his car and apologized, saying, “I really think I’ll regret it if I leave.” He said he would come back to pick me up for dinner. He got lost on the way to my apartment and I tried to give him directions over the phone. We went to a Thai restaurant where he asked me what he thought the role of women in marriage was (I got the feeling he had a “men are superior” thing going on), and also this question:

“Are you planning on having alot of kids?”

“Um…no, why do you ask?” I said.

“I dunno, because you drive a Buick. Seems like the kind of car you’d buy if you were planning on having a lot of kids. Either that, or your grandparents gave it to you.”

“No, I bought this car myself.”

On the way home from dinner, he asked me if I would sing for him. It was awkward, and I said no. He asked again- “But whyyyy not?” (Because I don’t sing on demand if I don’t feel like it?) I said no. He dropped me off and went back to his hotel. 

He called me super early the next day to say he was coming over in 15 minutes. He sounded panicked. 

I had just enough time to throw on some clothes and comb my hair when I heard a knock at the door. He looked dazed, as if he’d just witnessed a horrific crime. He sat down on my couch and just quietly stared into space. I finally asked him what was wrong. 

What wasn’t wrong? Turns out he thought his hotel was extremely sketchy, the door to his room wouldn’t lock properly, he thought he heard drug deals going on outside his door and a gunshot outside his window. He hadn’t slept much. 

We decided to go to a nearby park and sit on the swings. He left shortly after. We exchanged a “good luck with your search” email, and that was that. 

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Indiana Jones

Hold on to your sweet tea, ladies, and meet Casanova, the airplane pilot from the South who hopped on a flight to come visit me. We went out to coffee for our first date where he told me I was “the One for him. I don’t need to look anymore.”

(Red flag or not?)

I was willing to overlook it for the time being. He wanted to take me to a steakhouse. I’d never heard of it but said, “ok.” 

It was a really expensive looking steakhouse. The hostess did a double take when she saw us walk in. I knew she recognized me, but she didn’t say anything. A decade and a half earlier and thousands of miles away in a different city, she had bullied me in school. The odd thing was, I had randomly seen her at a party a week earlier, where she had made a snide comment about my hair.

The look on her face– seeing me walk in with Casanova and ask for a table in a restaurant that she probably couldn’t afford to eat at– was priceless. I was secretly gloating a bit on the inside. (Not my finest moment.) The steakhouse ended up being completely booked, so we went somewhere else.

Casanova kept trying to hold my arm in the crowd of people that had gathered outside for some parade so that we “wouldn’t get separated.”

The next day when I called to pick him up from his hotel and get breakfast, he asked if I wanted to come up to his hotel room because he “had something he wanted to give me.”

(Red flag? Red flag.)

I stammered awkwardly: “Uhhhh…..no thanks, I’d rather meet you in the lobby….?”

The “something” actually turned out to be a necklace and bracelet, which was a very thoughtful gesture. But telling me I was “the one” for him, plus the expensive dinner, and then the jewelry was just too much for me. They were lovely gestures, but Casanova gave the impression that he was trying really hard to impress me and the gestures didn’t seem 100% genuine.  Breakfast was awkward. He went back to the South and we parted ways. 

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I wish Shakespeare, HD, Indy, and Cassanova the best. I don’t have any bad feelings toward them. Some people have success with online dating, but I decided that it just wasn’t for me– too many ups and downs. Having a connection with someone through emails and phone calls doesn’t guarantee that you will have a connection in real life. You can spend weeks trading emails and phone calls back and forth, only to know within five minutes of meeting someone that the connection just isn’t there. 

Was online dating a waste of time and money? I don’t think so. The relationships that don’t work out still teach us something about ourselves and what we are looking for in a person. Sometimes it takes time and distance to see the lesson, but it’s there when we’re ready to see it. 

With Shakespeare, I realized I needed someone who could open up in a conversation and laugh and be silly. With HD, I realized his extreme lateness and inability to commit were turn offs for me. (And looking back, I realize that I wanted him to be clear about how he felt, but I had let email conversations with other people fizzle out without being clear about “hey, I just don’t think we’re right for each other.” If I had to do online dating over again, I would try to be more clear about how I felt too.)

With Indiana Jones, I realized I needed someone who could be adaptable in new situations (and know when not to say something). With Cassanova, I realized that I needed someone who wouldn’t just rush into a relationship without really knowing me.

If you’re in the midst of online dating, ugh…I get it. It’s hard. Do you want to give up and never go back to it? That’s okay. At the very least, you’ll have insights and wisdom from it that you couldn’t have learned otherwise (and some interesting stories!). However, I know there’s this tension of, “what if I quit just before I meet the right person?” This could happen. But I tend to think that if part of the destiny of your life is being with someone, you’ll find them. That if you’re really meant to be together, you’ll find your way back to a person somehow. Pray about it, think about it, and see if you sense which way you should go with it. Follow your intuition!

Have you tried online dating? What do you think of it? If you haven’t, would you try it? Why or why not? Please share in the comments!

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The Highs + Lows Of Online Dating

* Some details (occupations, states, etc.) changed. 

* Indiana Jones image from imdb.com; Shakespeare and Casanova images from wikipedia.org




3 thoughts on “The Highs And Lows Of Online Dating”

  1. I never had any desire to pursue online dating, but your stories are priceless. I did have a blind date once, with some communication that followed the date, and…let’s just say there wasn’t a second date with that gentleman.

    Liked by 1 person

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