Relationships

10 Hilariously Bad and Adorably Sweet First Date Stories in Honor of Valentine’s Day

Some are A LOT better than others. 

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First dates are like a box of chocolates. You never know what you’re going to get. Sure, Forrest Gump didn’t go on many dates, but like life, they are filled with possibility. They can spark butterflies, excessive sweat, even second thoughts, because let’s be honest, dating can be kind of scary — but hopefully in a really fun, worth it kind of way. 

Single women of all ages, whether they have been married before and are new to the dating scene or are seasoned pros, are embarking on first dates with co-workers, the cutie from the coffee shop, or their newest Bumble match. Some end with a goodnight kiss and plans for a second date, while others end in less favorable ways — like escaping while your date is in the bathroom!

The one thing they all have in common? They make great stories. Bad or good, most women are happy to tell them… and we’re all ears. Here are some (shall we say entertaining?) first date stories to help you celebrate love, both lost and found, this Valentine’s Day.

A Little Too Sweet

“I was on a blind date and the guy ordered two strawberry daiquiris. He started acting very strange and I had to pull the car over (he was driving). Turns out, he was diabetic and had a serious reaction from all the sugar. I called an ambulance. The EMTs asked me all kinds of questions about him. Of course, I had no answers because we met two hours ago! The folks at the ER desk ask if I’m the blind date lady — apparently, word gets around fast! After sitting in the ER waiting room for a few hours, the guy asks ‘when can we go out again?’ Not likely! My friends will forever refer to this as my coma date.” –Ginny, 38

The Jokes on Us

“I met my husband through online dating. He was my first and only online date. I did my dating profile humorously and said I wanted to date someone who enjoyed songs about chickens or whisky. He happened to have an old 45 of his dad’s that had “Ain’t Nobody Here but Us Chickens” on one side and “Pappy’s Little Jug” on the other. We now have the 45 framed and hanging in our home.” – Jill, 51

Tired of You 

“I met up with a guy I met online at a local bar one day after work. Turns out, he was a medical resident who had been awake for over 35 consecutive hours. He showed up in his dirty scrubs and apologized in advance for being ‘a little tired.’ We ordered a couple of martinis and did the usual small-talk. When I returned from using the bathroom, his head was on the bar and he was fast asleep. I left a $20 on the bar and snuck out before he woke up.” – Abby, 24

Ready to Play Ball

“We were supposed to go to the movies, but at the last minute he called me up and said, change of plans, how would you feel about going to the Red Sox game? I kind of felt great about it. So, he picked me up and we made the two-hour trip to Boston. After the game, we hit the bars for drinks and dancing. Our first date lasted about 12 hours because we were having such a great time together and we didn’t want it to end.”  – Suzanne, 41

Karma Chameleon

“I met a guy online and we decided to meet up at this local club on a Friday night. To be safe, I brought a group of friends. [I saw my match] and I was immediately turned off. When he walked up to our table asking for a Cailin, I said, sorry no one here with that name. He was a little flabbergasted and hung out at the club for a bit after that, but luckily I never saw him again. Karma got me back on another date when the guy said he was getting something out of his car while I was cooking dinner… But he never came back!” – Cailin, 28

Request Denied

“ [A client met her match] for drinks at a local bar and she said she knew right away that he wasn’t someone she was going to be interested in. He talked incessantly about himself, only turning his attention to her to comment on how great her body looked. After one drink, she made an excuse to leave. He followed up several times, sending texts about seeing each other again. She ignored his messages hoping he would take a hint. Then, a Venmo request [arrived] asking her for her to pay-up for her drink!” – Jess, Dating Coach

Porcelain Gods

We went to dinner and a night club and I ended up drinking way too much. We went to his place and I was so [nauseous]. I went to the bathroom and was getting sick and he held my hair back for me. We went to sleep on his sofa and he did NOT try anything. He was a perfect gentleman. Five years later we married and we have been together for 39 years, married for 34.” – Cindy, 62

Mama’s Boy

“I met a guy online [and when we went out] for burgers and beers there were two people he couldn’t stop talking about: his mom and his ex-wife! He whipped out his phone to show me pictures of both of them. When the waitress came to clear our plates, she asked if I wanted to wrap my leftover food, to which I replied, no thank you. The waitress was about to clear my plate, when he reached over aggressively and said, I will wrap it, Mom will love that!  I could not get out of there quick enough.” – Stacy, 37

Sister Act 

“My worst first date involved a guy who kept calling me by my sister’s name and admitted that he really wanted to be out with her, not me. He also intentionally put a glop of ketchup on his cheek, looked at me and said, is there anything on my face? I wasn’t laughing.” – Barb, 35

Close Encounters

“I went out to dinner with a guy I met on Match. We went to a nice restaurant and he proceeded to sit next to me in the same booth and kept playing footsie with me under the table. All the while, he couldn’t stop talking about COSTCO and how much money he saves by shopping there. Longest hour of my life.” – Jaime, 36

Say a Little Prayer for Me

“I met my husband through a Christian online dating site 24 years ago! Online dating was in its infancy at that point so we were both very hesitant. We had actually been talking and emailing for several months before we met in person. Due to my fear that he was some weird serial killer, I made him meet me at church for our first date. Our 20-year anniversary is this June, [and we have] 2 teenagers.”- Amy, 49

And there you have it, folks. A big box of chocolates and only some are worth a second bite. But I will tell you one thing, if you put a big box of chocolates in front of this single lady, I am digging in and taking a bite of each one. If it happens to be one of the nougat-filled surprises that I despise, I will simply throw it out and keep looking for the truffle. Because I love a good truffle, a great adventure, and a first-date worthy of a story.

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