I have been on some good dates and some bad dates, clearly, but recently, someone asked me what the best day I’ve ever been on was. So, I thought that I’d do a quick little post about the best and worst dates I’ve ever been on – the top three for each – and go into a bit more detail about each of them, even for the ones that you might think you already know everything about. 

For the record, these dates are not about the person, necessarily. I’m strictly going off of the date itself. The person will definitely play a part in it in some instances, but even if the person turned out to be an asshole AFTER the date discussed, it could still be considered a good date. It’s based only off of that particular date. 

Let’s start off with the bad, shall we? I mean, I am an optimist so I do have to end on a good note.

While I have certainly had my share of bad dates ( I mean, I had to create a whole “One Hit Blunders” series to talk about them) the following three stand out as being the top three worst ones.


Top 3 Worst Dates

3. Brunch with The Cancer

After our first date, which as a reminder was drinks at Tavern in the Square and then around Faneuil Hall, PJ invited me to brunch at Rosebud. While the food was good, the date was not. 

I remember being a minute or two late, as I usually am, because I was having trouble getting an Uber and the way he made me feel about it was like I had just held up his entire day. I fully get being annoyed when someone is late – it drives me crazy when my friends are constantly very late for things – but it was just a minute or two, and I told him right away. So, that kind of bothered me but I tried to let it go.

As the date went on, I remember realizing that we just weren’t very compatible. He kept talking about really weird things, and then would just kind of give me this borderline creepy stare as he waited to see my reaction to it. He also told me that he sleeps with the temperature on 60 DEGREES. How is that even possible? I like it a bit chilly but I think I’d actually freeze to death if I did that. 

But, really I just think that in general “eating” dates are overrated and not what I enjoy. I don’t like having to feel like I need to be super conscious of what I’m eating, and if I’m being a messy eater, and it’s hard to have a conversation over food. Even though I’m not a big drinker, I’d rather do drinks first because at least it’s easier to talk. 

Also, after brunch was over I was talking about what else I needed to do that day clearly sending the hint that I was done with this date and ready to go home, yet he convinced me to go on a walk even though it was starting to rain, and then insisted on driving me back even though I was perfectly fine calling an Uber. Sometimes things cross the line between polite and possessive, and this was one of those times. 

Overall, it was just very weird and why I agreed to a third date after that, I don’t know. It was just weird, and when I think about some of the worst dates I’ve been on one definitely makes the list.

2. Japanese with The Dollar Man

Not only was this a food-related first date, which I’ve already said I’m not into, it also involved us sitting next to each other which is one of my biggest pet peeves with couples in general – how do you talk like that? 

Obviously, it’s required at a Japanese steakhouse, and I do love Japanese food, but still, it just makes for a very awkward first date when you’re half talking, half watching someone cook your food. Overall, it’s just not the ideal situation for a first date. 

Add this is with how much he talked about me offering to split the bill, and how intimidated he seemed to be by me the whole night, and it just turned out to not be one of my favorite dates. Plus, he took my leftovers which I think is kind of weird, and I just never heard from him again afterwards, so why spend so much money on a first date if there was never going to be a second one?

  1. “Hot chocolate” with The Creepy Catfish

Did y’all really have any doubt that this would be the worst date I’ve ever been on? I’m not sure if it was the part where he tried to hold my hand and yelled at me when I didn’t want him to, or when he literally backed me against a tree and got in my face, or the whole bit where he told me I was “too fucked up” to love, or when he basically insinuated that I couldn’t make him leave my apartment because he’s bigger than me that sealed the deal, but no matter what, he definitely takes the cake. 

And that’s not even including the whole part that he – one, showed up over an hour late to the date that he planned and, two, changed the date from bowling to hot chocolate and wouldn’t even bother to take me to a legitimate place for a hot chocolate. I like to be at least somewhat courted, and Starbucks is not going to cut it.

Top 3 Best Dates

3. Halloween Horror Nights with The Vegan

As I’ve said before, I really like doing activities or going to special events on dates, and this one stands out to me because Halloween Horror Nights is not something you can do just anywhere. 

As I said in his chapter, I am a huge scaredy-cat. I scream like I’m being murdered at the slightest jump scare, but he sucked it up and powered through the night. He went first into EVERY single house, let me hold his hand and bury my head into his back while he pulled me through certain parts, and was so sweet. Even though I definitely almost ditched him at one point running from guys with chainsaws, this was just a really fun first date activity if you’re into spooky things which, despite how scared I get, I do like.  

It’s also a really great way to weed people out – if he told me to suck it up and didn’t care that I was scared half to death, I wouldn’t have liked it, and if he decided that my swearing like a sailor wasn’t his thing, then at least we figured that out right away, right?

2. Hiking with The Rollercoaster

I liked this date because it was the first time I’d ever done a big hike (which I totally lied about to both impress him and make him not feel like we couldn’t go hiking because I wasn’t that experienced) and it was such a beautiful place to have been my first “big” hike.

It was an activity, always a good thing, and it was also something you can’t do everywhere (you can’t go hiking in Florida, really) and something that was also a good challenge for me. It was fun experiencing something new with someone I cared about, and I just really like to be outside.

The views made it even better for sure, and I liked that at some parts we talked but at other parts, we just let each other enjoy the whole situation and have some silence that wasn’t awkward or weird at all – I feel like that’s always a big thing if you can be quiet with someone and it’s not weird. 

Overall, this was just a really fun and exciting and adventurous date and it’ll always be one to beat in my eyes.

  1. Bowling with The Cheater

The absolute best date I’ve ever been on was bowling with Al. It was the perfect mix of time talking and time doing something fun together. It was the right idea to have a drink or two first to get to know each other and loosen up a bit (and have the bartender comment on the fact that this was our first date) before moving into the next portion of the date.

I definitely liked that I beat him at bowling, and I’m also just weird and love bowling. The conversation flowed, which is important to me, and we had a great time at every part of the date. It is kind of weird looking back and thinking about how much chemistry we had right off the bat knowing what he was really doing. 

It doesn’t hurt that the date ended with us going to Trader Joe’s so he could buy me wine and guacamole, and then him making me tacos while I pet his cat, but I think that even without the tacos this would still be my favorite date I’ve been on. It’s also the longest first date I’ve ever been on – I think we met at Lucky Strike at about 3:30pm and he drove me home from his place at like 2:30am. I only remember that because we almost got Tasty Burger but then we realized it was closed. But I was still hungry, and I also needed something from the drugstore, and for whatever reason at nearly 3am it seemed like THE most important thing to get, so after he dropped me off I immediately called an Uber and went to a 24 hour CVS near me to get it… and some frozen mozzarella sticks because it was too late for Domino’s delivery.


So there you have it – my top three best and worst dates! Tell me about yours – what are your best and worst dates you’ve been on?

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