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Understanding in Hindsight; Faith in the Future

Updated: Jun 23

Five Things I Learned from Dead-End Dating


It’s officially #SummertimeChi, the time for convertible car rides, packed patios, and outdoor date nights. After a long and somewhat lonely winter, I’ve decided I want in on that action, too. Even though the past few dates I went on didn’t unfold how I’d hoped, I did learn something from them. Here’s what I’m going to take with me as I cruise into this next season of (hopefully) love.


1. Chemistry isn’t everything.


They say when it comes to that spark, “You’ll just feel it.” I can say from experience, this is true. At first.


I definitely believe attraction can grow over time, especially when you start as friends or celebrate an arranged marriage. But when you go out with someone, I think you can tell if there’s an attraction within the first date.


This happened to me twice. Our chemistry was undeniable within the first 45 minutes of talking. Minutes turned into hours, and polite smiles turned into giddy laughs. I felt like a teenager again. Those first dates were exciting, magical even. I was lucky enough to find myself in the middle of a 2000’s rom com… but it wasn’t enough to get us to the “...and they lived happily-ever-after” part.


Over time, the initial excitement began to fizzle. Texts (on his end) became more sparse. I could sense his lack of interest in setting aside time to talk to me, and eventually, date me.


I’m not trying to make anyone feel sorry for me or take sides. I’m saying this because while I believe attraction is important, it can’t be the foundation for the relationship.


I can’t expect to keep my oil lamp burning without oil. A lighter without fuel only sparks for a second. It’s science. And it actually reminds me of a poster that used to hang in one of my high school science classes that said:

You can get by on charm for about 15 minutes. After that, you better know something. -H. Jackson Brown Jr.

In other words, the deeper your oil reserve, the better.


2. Be straightforward.


This has got to be one of my biggest regrets. I’ve beaten myself up about trying so hard to make a good impression, that I gave the wrong impression.


There were first dates where I purposefully withheld information about myself because I was embarrassed. But they weren’t things like “I’ve never seen Lord of the Rings” or “I like ketchup on hotdogs” (it’s a Chicago thing). These were deeper values about myself that doubled as dealbreakers.


You don’t have to learn everything about each other on the first date or two, but do talk about things like intentions and boundaries. I brought these up on a first date, and while I maybe came off strong, I don’t regret it, because even though he ended up ghosting me, at least I presented the most honest version of myself.


Being straightforward also means don’t ghost. Let me repeat that for those in the back: Do. Not. Ghost. You might think you’re being nice by not saying anything, but as someone who’s been both the ghoster and ghostee, trust me when I say that being clear about ending things romantically is healthier for everyone involved. It can be as simple as saying something like:


  • “I had a great time with you, but I’m just not feeling it.”

  • “I see us connecting more as friends.”

  • “I’ve enjoyed getting to know you, but I want to focus on _____.”


You can fill in the blank with “myself,” “my career,” heck, even “another relationship.”


Whatever it is, a little honesty will go a long way. And you’ll be respected for it in the long run.


3. Listen.


There’s nothing more impressive than when someone puts their phone away to talk to me. I like feeling seen, but even more so being heard.


One guy showed me this through little gestures, like making eye contact when I talked, waiting to check his phone (and smart watch) until a break in the conversation, and bringing up something I mentioned later in the date. This re-assured me he was fully engaged in the moment.


Active listening also frees you up to observe the other person better - mannerisms you may fall in love with, how they treat the waiter, body language, etc.


That last one is huge in helping steer dialogue in the right direction. For example, when I asked one date about his parents, his demeanor instantly shifted. This clearly wasn’t a topic he was ready to talk about on a first date, and I wasn’t going to force it. Because I paid attention to his non-verbal cues, we were able to change the subject and keep the conversation flowing.


Sometimes talking too much stems from nerves. I get that. I’m not great with awkward pauses, either. One time, I totally spaced out because I was trying to think of the next thing to say, but I think if I would’ve taken the time to just listen, it would’ve taken off the pressure I put on myself to carry the conversation.


4. Let People Surprise You.


I used to watch The Bachelor franchise season-to-season. And I would always cringe when someone said, “I was totally skeptical, until I met you.” Ick. Eye roll. Barf. Get that garbage outta here. Like, does anyone say that anymore? Turns out, I do.


Maybe it’s my past heartbreaks, or maybe it’s all those hours binging-watching The Bachelor, but my heart has learned to put up a very thick guard. I’m talkin’ brick wall with gates of steel. And my expectation was that only the perfect person could knock it down. That was the usual game I expected everyone to play. What a fun way to date, no?


Not at all. So, the last date I went on, I thought it would be fun to turn that game around. Nix my expectations. Keep my social media “research” to a minimum. Don’t read into it too much if plans change. Basically hold off on forming opinions until the first date.


And boy, was I surprised.


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What I learned is that people have two personalities: their real-life persona and their social media presence.


Trying to get a first impression strictly from pictures, texts, or app profiles doesn't give anyone a fair chance. Judgments form, consciously or subconsciously, and we see others through a filter, not for their true colors.


Does it bother me when people are bad at texting? Yes. But if I write them off before ever meeting them, then I may never get to experience the depth of their personality or sense of humor that really shines in person. And what a lovely surprise I would be missing. Let yourself be reverse catfished.


5. Wish Them Well.


After a break up, there’s nothing I want more than to get together with friends, trash-talk my ex, and scream “Someone Like You” by Adele at the top of our lungs. Oh, and make a video of it for social media. We want our exes to regret their mistakes. We want them to see how much better off we are without them. And we sure as hell want them to want us back.


Bashing is easy, normal, even therapeutic. But what if there’s a different way to handle a breakup or a bad date?


I’m going to give you the advice my spiritual director gave me: pray for them.


Have your Adele moment. Take the time and space you need to process whatever you’re feeling (for me, it was anger that morphed into confusion, then sadness).


After that, when you can finally start to feel your feet on the ground again, and the dark cloud around you begins to disappear, take that messy ball of pain you’re holding on to and toss it back to the person who created it. Think of it as your final send-off.


Only this time, send them off with prayers, good energy, and well wishes. They may not deserve it, but it’s the goodbye you deserved to have, and the closure you are worthy of, as you heal from a difficult, confusing season.



Dating can be hard. The lessons learned in hindsight come with their fair share of pain. Hopefully, these lessons can give you as much hope to keep trying as they now do for me. Let’s give ourselves permission to fully enjoy the adventure of our journeys this summer!



 



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