My 5 Best and Worst Dates

What makes a good date? Surprise, good conversation, a little romance, and some degree of superior making out. A bad date? That’s usually a combination of poor decisions and even worse chemistry. That said, some of my best dates were one-off affairs while some of the worst led to long-term relationships. I’ll leave it to you to guess which ones led to love.

My 5 Worst Dates

  1. The guy who started calling me by a name that was not mine because I had the same name as his sister, which just wouldn’t do. He called me Sam. That is not my name.
  2. Going to see The Blair Witch Project when I had said I cannot watch scary movies. I really wanted to walk out, but I was too afraid to open my eyes.
  3. The time I wasn’t able to take a sip of my wine before being kissed. Badly.
  4. The guy who claimed to speak Spanish and promised to take me to a Guatemalan restaurant that was really a fried chicken restaurant run by Guatemalans. I do speak Spanish and understood what pollo frito meant.
  5. A salmon dinner served with a glass of milk. Salmon and milk? Not a good combo. I have no idea why he didn’t just buy a bottle of wine.

My 5 Best Dates

  1. The guy who took me on a spring picnic for which he had home-cooked everything and purchased a bottle of some of the best wine I have ever tasted.
  2. Getting lost in Buenos Aires with a cute Canadian.
  3. Going to the opera and not really watching the opera. It’s like making out at the movies, only classier.
  4. Two days spent on an island in the middle of a giant lake in Canada on which the previous campers had left behind their hammock.
  5. A whiskey tasting. Scotch is one of my favorite things. Combine that with a cute companion? Heaven.

So tell me, dear readers, what are your best and worst dates? Did they lead to love?

By [E] Sally Lawton

My food groups are cheese, bacon, and hot tea. I like studying cities and playing with my cat, Buffy.

9 replies on “My 5 Best and Worst Dates”

Worst date: The guy I was seeing on my 21st birthday was living in another city for an internship, but (after WAY too much coaxing) came into town for my birthday. He couldn’t stay for my actual party/bar hopping session, but he said he’d spend the afternoon with me. We were both broke, so I suggested a walk to a nearby park and then go to dinner somewhere cheap. He showed up late, hungover, and in the same clothes he’d been wearing for the past 3 days, as he’d apparently come into the city 2 days before he said he would and spent that time partying with his friends. When we went to the park he barely said anything to me and after 20 minutes wanted to go. I said ok and then he asked which coffee shop I wanted to go to. Confused, I suggested a couple places to eat, and he then told me he didn’t have the time because he had to go home and eat dinner with his parents. I told him to just drop me off at home, and then he didn’t even kiss me when he left. I sent him an e-mail (our primary mode of communication) saying I didn’t really appreciate him being so crappy on my birthday, and then he responded while I was out barhopping, dumping me with an e-mail full of bad prose it would embarrass a 14 year old emo Poe-wannabe.

Best date: I’ve had a lot of good dates, but my most recent favorite was a dinner and movie “date” I went on with the guy I’m platonically seeing right now (it’s complicated). We went to Red Robin, spent most of it laughing, got told jokes by a hilariously dead-pan magician, and laughed hysterically when I missed my mouth and spilled coffee down my shirt.

Worst date: After dinner we meet up with a group of people at his friend’s house. I had driven us to dinner and the friend’s house but at the end of the night he rode home with one of his guy-friends who was there. It was winter and one of the biggest snow storms year. I was left to dig myself out of the parking lot and drive home alone, in the blizzard.

Best date: My current boyfriend took me seriously when I said I didn’t want to do anything for Valentine’s Day. No fancy dinner, no presents. We ended up having dinner at Fazzoli’s, because he figured we should at least do something together that night.

Worst date: Double date where both guys kept leaving  the table to take phone calls.  After we ordered appetizers and entrees and were on the second round of drinks they said they had to leave because their friend got a DUI. The left us $40 at a nice ocean view restaurant for their share. An older couple next to us asked if they had to leave because they were doctors on call. They weren’t. The husband was more upset than were and said men don’t know how to be gentlemen these days. Our waiter was also perplexed but we decided to enjoy our dinner anyway. When the check came it turned out the couple next to us had paid for us and encouraged us to have dessert!


Best date: Very romantic dinner on Valentine’s day,  a handmade Word With Friends card and Burt Bacharach concert!

Well ‘luckily’ (depends on who you ask), I only ever dated two guys. One was my worst date, the other has been my boyfriend for the last four years.

Number one was silent, gave me the feeling he kissed me because he thought that was supposed to happen, didn’t talk at all about what we had done and turned into a stone wall after the date when I wanted to talk about everything that had happened.

One of the dates with le bf was in a zoo, the other in a book store. Those things are like my natural habitat.

Worst date: We played mini-golf. I had let him know in previous cconversations how seriously I take my mini-golf. He let me win and then kept reminding me that I only won because he didn’t even try. Then we grabbed coffee and desert and he was rude and condescending to the waitress. I faked a migraine and made him take me home.

Best: First date with future Mr. QSS. It lasted 8 or 9 hours and included a backyard kegger, The Simpsons movie, dive bars, and making out in a parking lot. And it wasn’t until after the movie and before the dive bars that we decided that it was a date.

Worst date: This guy snuck off to the bathroom three times during dinner to snort cocaine (I’m assuming it was cocaine) then stuck me with the bill. After dinner he had the gall to try and get himself invited back to my place until he finally told me that he really needed a place to crash that night. The was the last time I tried internet dating.

Best date: a tour of a meadery and lunch that melted into window shopping at an outdoor mall until dinner time after which he invited me dancing until midnight and we rounded off the night stargazing from the back of my car.

Worst date: Drinks at Applebee’s (I worked late and was too tired to even care), and the guy did not say three words to me, except he brought me roses when beforehand, he had asked if I would like roses and I said “no thank you” and really meant it. Afterward, he texted me and told me he was just so taken with my beauty. Okay, fine, but that doesn’t change the fact that you went out with me and didn’t speak to me the whole time. Other worst date: a guy who had was part of our larger group of mutual friends who proceeded to tell me how much more fun it is with everyone else there. This was after the previous weekend, when I had driven him home from the bar and he threw up in my car.

Date that was the best until he did something stupid: My current boyfriend took me on our first date three months after we started our relationship. After a totally nice dinner at an adorable restaurant that was so romantic and fun and we had the best time, he wanted to go to this place in Old Town, and along the way, made us go pick up another couple that I didn’t know, so they could join us. I was not asked about this, nor was I pleased. It took another year for me to be able to tell him how irritated I was, and that if I didn’t like him already, that would have been the last date. I’m glad it wasn’t though, because our 2 year anniversary is next week and I’m super happy!


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