Build. Hack. Play. It's just what we do.
Build. Hack. Play. It's just what we do.

Most of us don’t have date fails in high school. High school is kind of a closed community, and you pretty much know what you’re getting into when you either ask for or accept a date. And you have plenty to talk about, because you are both part of that community.

No, the date fails begin in college and beyond — and we’ve all had them. We end a relationship and decide to get back into the dating scene after a reasonable period of saying, “No, I’m just going to stay single for a while and improve my relationship with my cat.”


Finally, though, you are ready. Friends, who have guys or girls they think are perfect for you, set you up; co-workers do too. Or you decide to take the plunge and try a dating website or two. Then the fun begins.

Learn From My Stories

I had moved to a new town for my dream job. I got settled in at work, in my new digs, and, about two months into this, I decided to take the plunge, accept the efforts of my co-workers to set me up, and just put myself out there by joining some dating websites.

I put up my profile with a photo I had professionally made. OK, so there was some airbrushing going on there, but it was a reasonable facsimile of what I might look like if I spent several hours at a spa and hairdresser. It wasn’t long before there were several “flirts” — that’s the term for a message from someone who is interested. This is all quite an ego boost, to be sure.

Finally, I took the next plunge and agreed to meet a guy after work at a small bar. And this is where the horror tale began. The rest of my stories will be divided into pieces of advice that are provided totally free of charge.


Tip 1: Be Honest When You Post a Photo on a Dating Site

I fully admit that my photo was a bit “touched up.” But his? I can’t imagine what miracle worker did that makeover job. It was like his photo was of a twin brother who was the more fortunate one when the genes were passed out. Even his teeth were different! I am not one to judge looks too harshly, but the photo job screamed dishonest — and that was a huge red flag for me.


The moral: A little retouching might be OK, but your date should be able to recognize you from our photo.

Tip 2: Stop With the Personal Questions!

The first questions out of this guy’s mouth, I kid you not, were as follows:

  • “What time do you get up in the morning?” What??? In my head, I am thinking, this guy is planning to call or text me just to say “good morning” tomorrow — now that’s a bit creepy.
  • “So, do you plan to have kids someday?” In my head: “Yeah buddy, with anyone but you.”
  • “How much do you make at (name of company)?” In my head: “Enough to remain single and support myself forever.”
  • “Who are you voting for?” OK, I’ll bite on this one. I respond. It’s a presidential election year, so I name my preference. Uh-oh. He’s voting for the other guy. Now, I can listen to 20 minutes of why his choice is better than mine. He rambles; I nod and order another glass of wine.
  • “What religion are you?” Really? This guy needs to get online and research at least some basic conversation tips for a first date. I wonder if I tell him I am a member of a devil-worshipping cult, he’ll leave. But lest that end up all over social media tomorrow, I name some uncontroversial Protestant sect that no one could find issue with. Pause. Uh-oh. Now he wants to know if I take the story of Lot literally. Lot? Who’s Lot? This is not getting any better. Time to shut it down.

I excuse myself to go to the restroom. While there, I call a co-worker, explain the situation and ask her to call me in five minutes. The phone rings. All my date hears is “Oh no! I’ll be right there!” Bingo. My best friend’s apartment building caught on fire and everyone has been evacuated. She will need to come stay with me, and I have to go let her in. So sorry we’ve had to cut this short. I throw the money down on the table and I’m out of there.

The moral: If you get too personal too quickly, your date is going to be creeped out and run away, just like I did.


Tip 3: Don’t Lie, Even in a Small Way

Another “match” from a dating site started out OK, but I learned a lesson here, too. This one wanted to take me for dinner at a really upscale place — OK, this is a good sign. Or is it?


We meet at the restaurant, and there is another good sign — he looks like his photo, which was pretty nice. He also ushers me in as we follow the host to our table and sits right next to me, not across the table — good sign!

Over a drink, we talk about our jobs and our day — the perfect ice-breaking questions. From his profile, I already knew he was a mortgage broker, so he tells me funny stories about some of his clients, and we are laughing together — good sign! Because I am a “behind the scenes” investigator for a local TV affiliate, I too have some good stories too, and he listens attentively — good sign!


The meal was wonderful, he saw me to my car and asked to see me again — we made a date for the following Saturday. Good sign!

The next day, I am excited to tell my closest friend at work about this great date with this mortgage broker. “Who?” she says. I told her his name. She bursts out laughing. “He’s a friend of my brother’s from high school, and he is no mortgage broker,” she tells me. “He works in a mortgage office, but he’s the guy they pay to go to the court house every day and do property title searches. I can’t imagine how he afforded to take you to that restaurant. I think he makes about $12 an hour.”


The moral: The world can be a pretty small place even in a mid-sized city. And what is the point in lying about anything? At some point, if you keep dating, they’re going to find out anyway. There is no long-term relationship to be had if you start out with lies.

Tip 4: Don’t Over-Drink, Especially on Your First Date

This next date story may have been the worst. When I was in college, I spent a summer in Washington, D.C. as a summer intern — I was a journalism major and got a position with a small news agency that basically got the political news and sent it out to news outlets in small towns across the country. While there I met another summer intern — he was working for a small law firm and going back to finish his last year of law school at Georgetown — pretty impressive.


One day he stopped by the agency office and asked if I was free that evening. He had just been given two tickets to a political fundraiser — free drinks and dinner, and the chance to maybe meet a congressman or two. How exciting!

I spent a good two hours getting ready for that date. He picked me up in a Lincoln town car (one of the law firm’s partner had loaned it to him), and we were off. For one night, I was going to be a part of D.C. society!


The evening began well. There was an open bar, and I indulged and actually had two drinks instead of my normal one. My date, on the other hand, was a bit of a lush. The open bar was just too much of a temptation I guess. Anyway, we finally sat down to dinner (unbelievable meal), and made small talk with the others at our table. The tables were cleared and the speeches began.

They were a bit on the boring side but I looked over at my date, and he had fallen asleep with his head down on the table. It was embarrassing, but I just sat there and pretended to be interested in some co-chairman of some part of the party. And then it happened. He began to snore. Not a soft snore either — he was really “sawing” away and tables around us were staring.


I had to wake him up, so I began to jostle him. Finally, he lifted his head up, looked around and proceeded to vomit all over the table. Everyone got up, including me. My next stop was the front door where I asked for a cab.

The moral: Never over-drink. The results can be pretty disastrous. In this case, I was just thankful that no one knew me, and I could exit quickly. We worked in the same building the rest of that summer, and he avoided me like the plague — I had no pity either.


Thankfully, apart from those disaster dates ,I actually had many great first dates, lots of second dates, and am now in a long-term relationship.

Bonus moral: Sometimes you have to “kiss a lot of frogs to find your prince.”

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