Tinder Time

Photo by cottonbro on

After escaping from the clingy text me tomorrow guy, I was starting to get fed up with online dating and was really tired of the mediocre prospects that I seemed to be finding. If I’m going to pay for an online dating service, I’d like to at least go on a decent date every now and then. So I decided to take a break from the paid for apps and give some of the free ones a go. With the explosion of online dating since I first began this adventure, the free apps had seemed to shed a bit of their hookup reputation and at least offered a bit of a chance at finding more than a one night stand. And at a cost of $0, I didn’t have much to lose.

I had tried Bumble before, and although I don’t have a problem being the one to start the conversation, I had never had any success there. I was never really into OK Cupid, so I jokingly made a Tinder profile one day. Of course Tinder probably has the worst reputation for being a hook-up site, but it had evolved somewhat, and from the profiles I saw at the beginning people were being pretty clear about their expectations.

Swipe Right

Still I didn’t go wholeheartedly into it, but when I was bored I would swipe through a few profiles and see what happened. One guy who I shared a nice conversation with mysteriously stopped messaging me after we discussed what we were looking for even though we both said we were looking for a potential relationship. Then, I happened upon Chris one day. He was 27 which is a little younger than I was going for, but I’ve certainly gone for that before so might as well give him a chance. He looked a little nerdy, but had a nice smile in his photos. He claimed to be looking for a relationship and worked for the school system in a nearby county. He messaged me after we matched and so we began to chat.

We exchanged a few messages upon which I learned that he was a custodian at a middle school, a cook at a local restaurant, and a self-proclaimed handyman. A jack-of-all trades you could say. His dream was to have his own business fixing things. Not exactly my dream guy occupation, but it sounded like he had some ambition and good skills. Chris also dove right into some of the big questions like how long it’s been since my last relationship and if I have any kids. Clearly a sign that he’s had things go wrong in the past surrounding these areas, but it didn’t make much of a great way to spark a conversation. Still I can empathize with being burned, so I answered his questions and hoped we could continue on to something more exciting.

Unfortunately, we seemed to get a bit stuck with the “How’s your day going?” narrative for a few days with not much other progress. Then out of the blue, I get this message.

“So would you like to maybe do something sometime?”

Wait- is this his way of asking me on a first date?!? Sigh. I can already feel this one spiraling in the wrong direction.

Still, I was willing to meet him in person because that’s really the best way to figure things out. Plenty of guys are not great at messaging, but can be decent in person.

So I agree to do something sometime, and ask what he suggests. His idea of something is a dinner which pulls up a red flag as it forces me to break my first date rule. Never agree to a meal on a first meeting. But after looking at my weekend schedule, it seems that might be the best option, and at least he’s suggested an actual something and not just left it up to me to decide, so I go with it.

Decisions, decisions

But then comes the difficult decision of where to eat. Here’s a tip if you’re planning a date. If you’re going to suggest a meal, maybe ask the person what types of food they like first. Then come up with some suggestions based off of that. If you still want the other person’s opinion, give those suggestions, but please don’t go round and round asking them to decide, but then knocking down their suggestions and picking your own choice instead. After going round and round, we finally decided on Red Robin Saturday at 6:30. Fingers crossed that the date goes better than deciding where to actually have it.

He asked if I wanted to meet him there or have him pick me up.

I politely said we could meet there as I didn’t have the heart to point out that allowing him to come to my apartment and getting in a car with a random stranger is a hard pass. Another helpful tip for all you single guys out there. No matter how chivalrous you’re trying to seem, asking to pick up the girl on the first date immediately ups your chances of being a creep.

Date Night

So off to dinner I go. I got there first and walked inside. I recognized Chris as he entered from his profile pictures, but instead of introducing himself, he just sort of walked up near me and looked around. “Are you Chris?” I asked. He looked surprised, so for a moment, I thought maybe I had the wrong guy. So again I said “Chris?” and this time I guess it registered because he said hi. And that was all. Cue awkward silence as we wait for the family in front of us to get seated. We get a table tucked in the corner and have a seat.

Now on most dates, I find it difficult to really look at the menu and make decisions about what to order because I’m too busy with getting the conversation flowing and getting the nervous chatter out of the way. But not with Chris. Here, we had radio silence. His eyes are looking around everywhere but at me, and he’s not saying anything. So I start tossing out random questions as we peruse the menu hoping to find a good conversation starter. Sadly, we seem to get stuck on simple one sentence answers. I’ve been on a lot of first dates and met my share of awkward or quirky guys, but never have I experienced silences so awkward as this date. Here’s a fun selection of some of our conversation snippets

Me: So do you like sports?

C: Not really. I mean I will go to a game, but that’s about it.

Me: So what do you like to do for fun?

C: Hang out with friends… and uh… not much really. I have a boring life. (Super. Just what your date wants to hear.)

Me: So do you like to watch movies or TV?

C: Well I don’t really watch movies unless someone else is around, but I have a projector and big screen. Also, I don’t really watch TV except the weather channel.

Me: Oh, well at least that’s very informative. 

Me: Do you like to travel or had any recent vacations?

C: Haven’t gone on vacation in over 10 years. You?

Me: Well I take at least 1-2 trips just about every year. 

Me: What are some places you would like to travel?

C: Alaska and Canada. 

I was mildly shocked on that last one that he actually asked a question back of me and our exchange on that topic lasted more than two lines.

It was becoming painfully obvious that Chris and I didn’t have much in common. “I promise I talk more once you get to know me” he said at some point. ‘Oh that’s good” I replied. … birds chirping…

Luckily our service was speedy and it seemed like this painful experience might be over soon. I took a quick peek at my phone as we waited for the bill and saw that I might make it out within an hour. But then Chris asked if I want to go do something else after this.

“Well what would you like to do?” I ask. “I don’t know, anything,” he replies. Ugh…. Somehow I’m not able to politely decline, and we settle on going to a nearby lakefront where there are places to sit and chat or a walking path. There is also usually some type of band playing on the weekends, so maybe at least something will entertain me this evening. I try to give Chris directions as he has come to my area for this date, but he still seems pretty unsure of where to go (It’s called Google Maps man!) so I offer that he can follow me. We walk out to his car which is a tricked out Honda Fit. I guess that’s what happens when you wish you had a sports car, but you’re on a jack of all trades budget.

As I drive to the lakefront, I desperately text a friend to see if she can help get me out of this awful date. She’s out to dinner with family, but offers to call me with a fake emergency if needed. I feel bad stooping to this level, but this date has been so boring, I’m really not looking forward to spending more time with this guy.

Date Night Part 2

We arrive at the lakefront area, and we are walking by the Whole Foods which is right next to it, and he says “What’s that, like a grocery store or something?” Me (dumbfounded)- “You don’t know what Whole Foods is?” (In my head- do you live under a rock?) 

Luckily there was a nice bluegrass band playing, and lots of people around so we picked a spot on an empty bench to listen to the music and continue chatting. I decided that I would give this about 20 minutes before I faked being really tired and needing to get home. As we sat, there was still a load of awkward silence and no connection brewing. Also, being closer to Chris now, I could see that his teeth were slightly yellowed. Most likely a sign of smoking or poor hygiene. Either way, not in the least bit attractive.

As it was clear that this date was not gaining steam, I faked a few big yawns and made my excuse about not getting much sleep the previous night so I needed to get home early. As we walked to our cars, Chris asked about another date, and I kindly declined mentioning that I didn’t feel much of a connection beyond a friend. I thanked him again for dinner and headed my own way. Of course he texted me later saying that I should give him more of a chance because he’s just really shy at first, and asking for tips on how to be more successful with dating because obviously it’s not going well for him. I tried my best to give him some pointers without being rude. Hopefully he took some of those suggestions for his next date.

So my experience with free dating apps wasn’t starting out much better than the paid ones. I gave up on Tinder pretty quickly after that. There’s got to be something better out there.

Until next time,


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