5 Girls Reveal Their Best And Worst First Dates

5 Girls Reveal Their Best And Worst First Dates

Over the years I’ve learned that I’m not an advocate for dating in the traditional sense.

Every now and then, though, there is a perfect stranger that enters the picture and changes my mind. The best first date of my life so far had little to do with what and a lot to do with whom. After weeks of witty texts here and intellectually stimulating texts there, I got really real with a guy I met through online dating and said to him,

“If we don’t meet in person soon, I’m going to throw in the towel.”

I didn’t have an interest in getting to know someone through a mobile device. A week later, we were holding hands and walking the restaurant-lined path Peachtree Street gifted us with. He would proceed to tell me he’d never done anything like this before, he’d never gone on a real date, he’d never been so attracted to anyone…the latter mirrored my never. We ate burgers at the Vortex and – despite burgers being my favorite – we ignored our meals completely in lieu of being enraptured in our conversation of getting to know one another. It was beautiful and one of the few first date nights I can remember never wanting to end.


Worst dates have always been the exact opposite of experiences like that first date. The absolute worst first date I’d ever been on was with a guy I had known for a while. Perhaps reality couldn’t withstand the weight of expectations, but if I could personify a yawn, he would be it and the date itself would be that times 1,000. He had a laugh that rivaled a car engine stalling to start and halfway through our movie became obsessed with using his fingernail to pick popcorn from his teeth in the loudest way possible. It was disgusting. Afterwards, while we ate our meals, it felt like he was trying to sell himself to me versus experiencing our connection in the moment: My credit score looks like this, my adjusted gross income last year was that, check out my credit cards. Gag. Give me something I can feel. Move me. Otherwise, a first date will never turn into a second.

I asked other people to recall some of their best and worst date experiences, and their responses were nothing short of entertaining. Here’s what they had to say about their best and worst firsts.


I feel like my generation don't do dates as often, or at least, not in the sense of the guys paying. And now it’s so convenient, dating is almost obsolete. My best first date was my most thoughtful date to me. Bryson* took me to see The Jungle Book at a local drive-in. My date knew it was my favorite childhood movie and I learned later that he called weeks in advance to request the movie play for me at that drive-in. It was incredibly thoughtful and I will never forget it.

My worst date ever was fairly regular. We went to dinner and it was just boring. Or maybe I was boring. I don’t know, it just felt like time stood still and in the most unpleasant way possible. Dates are best to me when they are thoughtful and have genuine effort behind them. I don’t want just dinner or a movie, I want you to think about who I am and cater the date to me.

[Tweet "I want you to think about who I am and cater the date to me."]


It started with us taking the city in by riding the Ferris wheel. I’ve never been huge on them from back in my carnival days, but Atlanta had just installed their new tourist attraction and it honestly looked like no Ferris wheel I ever saw. It was different. My date and I played "Never Have I Ever" in our little bubble floating above the city. Afterwards, we did dinner at some five-star restaurant and stuffed our faces with five courses, ending with a crème brûlée that tasted heaven sent.

That best first quickly turned into my worst first after we returned to his car in the parking garage. His entire demeanor shifted from charming, sweet guy to shut down and cold. I was almost tempted to get out of the car and walk away. He explained to me that he had a lot going on in his life and was wondering if I would even want to deal with him after I learned the whole story. He lived with an ex and more than that, they shared a bed, and more than that, they had gotten into a physical altercation the night before which resulted in him punching her square in the stomach. Suffice to say, it was our first and last date and easily my best and worst first wrapped in one (laughs).

I like dates that challenge me and I think that’s what I like about the guys I choose to get into a relationship with. Put me on to something new, open my mind to a new perspective. But please, leave the ex in the past before you decide to ask me out. Seriously.



Is there a such thing as a best first date? I don’t know if I know what that looks like. With my ex husband, I have a lot of beautiful memories of the moments we shared when we first started dating. My cousin introduced us because we were both resource teachers traveling between two elementary schools. He and I enjoyed movies and dancing a lot - we were always in some nightclub dancing the night away whenever we could. The conversation was always easy, about any and everything.

My nephew set me up on a date that turned out to be my worst date. He described this guy to me: attractive, dark, over six feet. However, when I met the guy, he was nothing like I pictured or like my nephew described. He was a short guy, 5’8’’, had a jheri curl like it was 1993 – just not my type. I got all dressed up to meet him at this little Mexican restaurant, had some drinks, talked. I noticed immediately that he did not pull out my chair for me and that he monopolized the conversation to talk about himself and wanting to move to California. I had to buy my own drinks so of course he was too cheap to make our dinner date include dinner. Later on, my nephew told me of how he talked of me so positively but for me, that was a huge one and done. Next!

I don’t think a best date has to do with a specific place, I think it has to do with whether or not you connect with the person.

What have been some of your most memorable first date moments? What takes a date from good to great for you? Share with me your first date stories below!

*Names have been changed for anonymity

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