Getting Back on the Bandwagon… Again

man giving jacket to woman

Dating, Online Dating specifically, can be pretty awful, and sometimes, it can be amazing and exciting. I contend OLD is as good as the attitude you take into it—short of the obviously bad, rude, date. If you take it too seriously, you'll get annoyed and dejected real quick. Online Dating largely annoyed me and I took a shit attitude towards dating. Sure, I went on dates, but I was jaded, I often took it too seriously and too personally. I asked the same questions many other folks as: Why is it that the people I'm interested in are not interested in me? Or some variation of that question. If you're on it enough, it grinds your spirit into a bloody, pulpy, mess. It's not good for the ol' mental health.

Try Really Good

Recently, I decided to put myself back out there. It's been roughly six months since I've been with anyone sexually or dated anybody. Needless to say, I've been lonely, starved for a romantic connection.

When I put myself on the Online Dating Apps again (Tinder, Bumble, Hinge) I was going to be very intentional. For me, that meant, putting up a bio that is real, shows my personality, and a couple of key bits of info to let prospective beaus know my basics before matching. I wasn't going to be overly clever/witty for the sake of being clear. I let the world know what I was looking for (a partner), that I have a kid, and that I don't want any new kids from the factory (used kids are okay though), and no one-night stands. I didn't put that detail in my profile, it was more of a mental note.

I did some research on what photos to put up and made a damn decent profile, all I had to do was wait and see (and swipe or click the clicky pass button on Hinge).

In short, I put together profiles that took effort. I was thoughtful about what I had and about what I was looking for. I made it clear I wasn't a troll.

When Should You Take a Break?

The guy in this Tinder profile right here. The dude should take a break. It's clear he's given up on being intentional. Hey, I get it. Everyone hits their point but rather than spinning cycles and wasting your time trolling, use that time instead to refresh your perspective and do other things.

This is from r/Tinder and while it seems like I'm picking on him, it was clear from his comments (there were hundreds) that he was frustrated and hiding behind emojis and passive-aggressive replies.

You've Lost The Feeling

When you've lost your desire to try you're not helping yourself out and you're wasting your time (and other peoples' time as well. Again, take a breather for a bit and come back after a couple of weeks once you get your mind right. Dating while feeling down isn't healthy and does a lot more to harm your self esteem than you think.

Wading Through the Matches

No, I'm not a right-swipe all the profiles and let my penis sort it out kind of person. If I was going to do this right, it was worth it to take it more slowly this time around, read stuff, and be mindful on who I wanted to match with.

Here, I've written out some of my criteria here. Obviously, this is all subjective and everyone has their own taste. Here's mine…

What I right-swiped on

  • Profiles with an actual bio (which I read) that I found interesting. More than that, if they could express their personality and sense of humor in their bio is a big plus.
  • Age-appropriate women. For me, I go by half my age plus seven and I leave the age thing equal younger and older.
  • Women who had interests written out rather than red flags.
  • Absence of Snapchat/Insta filters.
  • Politically aligned, spiritually aligned.
  • Someone who was attractive to me.

What I left-swiped on

  • I feel like it's weird to say but I cannot stand profiles where someone starts off by saying: I'm highly intelligent, fun, loyal, caring, etc. People don't do this in real life but whatever works for them, I guess.
  • Bad photos, profiles with photos where the woman is wearing sunglasses, the photos are too far away, only has head shots.
  • They list red flags instead of talking about who they are or what they want. I think a couple obvious ones are okay but when it's your whole bio? Pass!
  • Profiles that have the energy that they clearly don't want to be there. Take a break then. We get it, OLD sucks. It's the game play it when you're up for it, take a beather when you're not.
  • People listing their Instagram or any other social media account. Pass.
  • People who don't live close or don't list their general location. Tinder has a particular issue in Los Angeles where there's tons of foreign women who pop-up and they're not necessarily using Go Global. At this point in time, I'm not up for doing long distance dating.

The Results

I received many more matches than I expected on all three dating apps. I had some good conversations, we were able to qualify one another to see if we wanted to go out on a date.

And then some of the conversations were just like this. Yes, that was the last thing she ever sent. Like, just say nah or unmatch them. Online Dating at its least finest.

The Matches and Conversation

I made a point to have conversations early and not let any convo linger. But I also was clear on what I wanted to do. Go on a date. If I liked someone enough through chat, I wanted to meet them.

I don't have a hard and fast rule about how many messages but I'm definitely not trying to have a PenPal thing going either. If I feel good about the chat, I'll ask them out. Hey, so, do you wanna go on a date with me? Super simple, whatever the context of the conversation calls for. I'm direct, I state that I want to go on a date. And if I'm not so sure if it's the right time to ask, I still put it out there. I say the same thing but then I follow up the ask with no pressure btw and I can match whatever you're comfortable with (video, phone). Lmk. In every case, my match agreed to the date.

Date One – Self-employed mother, 35mi away

There was no spark. We were able to have a good conversation though. She showed up wearing a simple black dress to this nice bar in the middle for both of us. It was clear pretty quickly that we weren't a fit, even though we were both having a good time. I was okay spending time with my date, getting to know her, even if there was nothing on the table. I wasn't looking for a one-night stand either. I paid for a couple of rounds of drinks and then we split the dinner bill later.

We hugged it out at the end. I sent a note on Bumble later that I had a good time but I didn't think there was a romantic connection, my date agreed, we still exchanged phone numbers and had lunch when she was up in my neighborhood last week! That was a good time but it reinforced we are not a connection.

Date Two – The Down-the-Road Gal, ~ 1mi

I live in a small suburb just outside of Los Angeles. No one lives here that is also dating, at least I've never seen anyone nearby when I'm on the dating apps. But I managed to find the one and only dame in my town. Our chat convo flowed, I asked her out, and we planned a fun date, looking up scary sites around LA before finally ending with dinner at El Coyote (where Sharon Tate had her last meal).

Our conversation was good, great even. But, again, that chemical reaction, that spark, it just wasn't there. Again, at the end of the date, we hugged it out and went our separate ways. Again, I messaged my date and told her I had fun but didn't feel a spark. She replied, I understand and promptly unmatched, which is perfectly acceptable. I would have wanted to try to be friends at least. But I understand why she might not want that.

Date Three – The Gal Who Sent Zero Signals

I wasn't sure how this was going to go. Our chat convo was warm, she was responsive, and she said yes to wanting to go on a date. I was thrilled because she seemed interesting and was such a cutie. But I couldn't get a feel for her level of interest. You know? Sure, text can be difficult to discern emotion, however, I usually pick up on things. I was getting almost nothing from her. I thought our date would be a cordial meet-up with a stranger, hug, and go our separate ways again…

I managed to lose my wallet as I was leaving. I spent twenty minutes looking for it. I messaged my date telling her I lost my wallet and apologized profusely. She didn't reply to my messages. So I kept looking for my wallet, checking my messages, too. Ten minutes later I found it, I got my shit together, and got on the road just in case. I messaged my date, telling her I found my wallet and was still willing to meet but that I was going to be about forty minutes late. My date finally wrote back, she was understanding, and still wanted to meet up, which was great because I was on the road by then.

With all the anxiety of being late and losing my wallet behind me, I got to the bar thirty minutes late and my date arrived just a couple of minutes after me. So if I'd been on time my date would've been thirty minutes late. BUT it didn't matter, it all worked out. We sat at the bar, near the end in a corner. There was one little man there, who bought us both our drinks for the first two rounds. He kept interrupting us, in between going outside to smoke a cigarette. During those times my date and I were actually able to connect and have an effortless conversation. Neat!

The man came back and tried to get the barkeep's attention by lighting his lighter, then he escalated into yelling, shortly after security removed him, with some fuss. My date and I carried on and had a lovely time.

At the end of the date, I tried to kiss my date, and she gave me a peck, and said sorry! look, it's the first date and the world is weird but I really, really want to go out with you again. Can I have your number? So I gave it to her, she texted me there, and we have plans this week for a picnic in her neighborhood.


Post Date Reflections

One trick I've picked up this year, talking with a therapist, and working on my mental health struggles, is that your thoughts are just thoughts, they don't represent reality. This is an important concept for me because, often, when a date didn't go anywhere, I would just unmatch and that would be that. And, in most cases, it's probably fine to do even after one date. But on each of my dates, I had a good time, real conversations, even with no romantic interest. Telling each of my dates how I felt was empowering and I noticed that my anxiety instantly disappeared. I feared that they would call me names, or tell me I'm a shitty person, or whatever, and it didn't happen. It was in my mind and it's a game-changer to say what you feel. Who knew? Literally, everybody, it turns out!

Dating With Intention

I know, it's hokey but it's also true. If you're going to try, really try, no half-measures. I think carrying on with Online Dating, with positive intent, has been helpful to keep me open-minded, even when things are stale or annoying. If I get to the point where I'm feeling dejected or upset, I'll just take a break and come back later.

Dating in a Reopening World

It's still a challenge to date in a world still fighting against COVID, learning to be more patient than usual is essential. In Los Angeles, being prepared to supply proof of vaccination is in full enforcement. Maybe it's different in your part of the world. Regardless, be patient, be understanding.

I'm Okay

I've previously written that this year has been a challenge for me. There have been moments where I've wondered if I would ever get myself settled and I've wondered whether I would, or even should, try dating again. A bit melodramatic? Yes, a bit. It turns out, dating has been perfectly fine and that I'm well on my way. I've had a couple of great weekends—a pair of great days (and dates). I'm doing well, I'm gonna be okay and so will you.

Author profile

Alex is the founder and managing editor at the Urban Dater. Alex also runs: DigiSavvy, for which he is the co-founder and Principal. Alex has a lot on his mind. Will he ever get it right? If he does, he'll be sure to write.

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