Things I Learned From My Worst Date Ever

Author: Maria Pappas, The Dating Game

Three years later, I still remember the worst date that I ever went on. I know, what a way to start a blog post about dating, right?

At this point, I don’t remember all of the nitty gritty details. But I do remember the generally awkward conversation, and being upset after it was over.

(I also remember that I ate a really great burger… still think about it sometimes).

But instead of letting myself wallow, I tried to learn some lessons from it so that I could look back with laughter instead of regret. I think it worked, so now I’ll share what I learned in the hopes that you can avoid making the same mistakes.

It’s harder than you think when one’s in college and one’s not
My date and I were in totally different places in life: I was in undergrad and he was in his first year of working postgrad. My schedule was varied, but it usually consisted of waking up at 10 for my 10:30 class, with lots of socializing time during the day. His consisted of waking up at 6 to get on a train from a different state to get to work in the city by 9. So no, I didn’t fully understand when he told me that he had a long day.

Sometimes, being in different places in life isn’t a big deal. But this time, it drew a divide between us. I should have thought about that before I sat down across a table from someone that I had almost nothing in common with.

If you’re not a drinker, don’t go to a bar. If you have to wake up at 5a.m. the next day, don’t go to a movie that starts at 11p.m. It sounds simple, but sometimes we will ignore ourselves or our intuition in the hopes of making a love connection.

Don’t settle for vagueness. Make solid plans
Our plan consisted of “I’ll meet you in *this area* when I get off of work.” AKA, I walked around semi aimlessly waiting for him, and then we walked around semi aimlessly together, looking for a place that wasn’t too crowded. And, if you’ve never done it, just know that roaming around an area you don’t know well with someone you don’t know well is usually awkward. If it’s not, maybe consider putting a ring on it?

If we’d had a plan, it would have started the date off on a better note. Not a frustrated “fine, let’s eat here.”

Now, I’m a generally old-fashioned girl who would appreciate if a guy planned the date, but if someone’s not committing, either: a) make the plans yourself or b) drop it. Anyone above the age of, I don’t know, 16, should be able to choose a time and a place to meet.

Don’t take things too personally
THIS IS THE BIGGIE. Like I said earlier, totally different places in life. So, yes, I thought that the work that I was doing as an RA was ~*groundbreaking*~ and I got upset when he poked fun at that. I was taking myself way too seriously.

Don’t set high expectations
For me, taking things too personally was a result of expectations I had made. But when you’re going on a first date, especially when you barely know each other, your expectations shouldn’t be too high. Obviously, have expectations, and don’t stand for being walked all over, but maybe don’t expect someone who will take care of your cat when you’re out of town. Or whatever people in relationships do.

But as my friends reminded me after the date, the whole thing just… wasn’t that serious.

They were there to remind me that there are worse things in life than a bad date. So I’m sharing that reminder with all of you.

Confessions of a Dating Disaster

Author: Mary Grace Donaldson, The Dating Game

Millennials, I’m about to let you all in on a little secret. While I don’t necessarily hope that you can relate, I’m willing to bet that some of you can.

I’m a dating disaster.

While I’ve been able to open up about some of my past experiences and personality quirks, it’s easier for me to write than speak sometimes and as a result, I’m pretty closed off. While I’m talkative with “adultier adults,” and with people I know very well, I also get nervous when meeting people.

Which makes dating… well, difficult.

I’ve been through a litany of disaster dates and situations — from the time that I completely embarrassed myself on a blind date, to the time I thought I was on a date but it was not a date… from unrequited love to “friends with benefits” to two failed profiles on dating sites while I was in college to making a dramatic exit from the fast-food restaurant where my college “boyfriend” (who may or may not have actually been my boyfriend) worked. And while it takes a lot for me to admit this, it gets frustrating.

Yes, I laugh about it. Yes, they all make for great stories that I tell with such dramatic flair when given the right audience that you’d think I’m performing stand-up comedy. Yes, I fully believe that there’s nothing wrong with being single… though I can list lectures 1-54 from my best friend on the subject of how I push people away and how happy he’d be should I manage to find a mate to the point that I think he’d wave pom-poms in my face. And what do I do? I stand there rolling my eyes.


But if we take all of the funny window trimmings away, sometimes, it’s a drag being a dating disaster, who either pushes away any potential mate who may get too close or who makes up scenarios in her head that will never ever happen… with the wrong person. My philosophy that it’s better to be upfront about feelings than to beat around the bush probably doesn’t score me any points in the wrong situation either — and my declarations of “I like you” or even worse, “I love you,” that went unrequited have not helped.

And you can’t help but wonder: is it me? Is there something wrong with me?

Millennials, I’m here to tell you that it’s normal to have that feeling. Your stupid, crazy and even hurtful experiences can truly shape your outlook to the point at which you can’t help but wonder if you’re the only common denominator in these situations. And I’m also here to tell you that such thoughts have not disappeared from my mind even as I write this.

But it’s also important to remember a few things when you have those thoughts.

Dating is different for us than it was for our parents. Not necessarily bad, but different. And it’s okay if you long for a dating world that you’ve never had — I know that I do. But it’s not you. It’s not even the other person you’re currently seeing or those you’ve dated in the past. It’s the dating world in which we live.

But, don’t give up, fellow dating disasters — that is, of course, if this is something you want. If it’s not, that’s more than okay. But if it is, don’t ever stop being who you are. Remember: there’s someone out there for everyone.