Tell Us Your Worst First Date Stories!


We answer your questions, so now it’s time for you to answer one. What was your worst first date?

Your worst first date could be an awkward online date or a blind date. Maybe it was a guy you never saw again, or maybe it was a terrible first date with the man you ended up marrying. Let me know!
To get you started, I’ll share a “worst first date ever” story of my own:
Many years ago, before I was with my girlfriend, I went on an online date. As is often the case with dating website, she wanted to meet somewhere neutral to get to know each other/make sure I wasn’t Christian Bale in American Psycho. Fair enough, I said, and we agreed to a bar. So I get to the bar and she’s not there. I wait a while, and then call her.
“Oh, we moved to another bar,” she says.
“Ah, okay,” I say. “Wait…we??”
Turns out she had brought along several friends and forgotten to tell me. Maybe she brought them along to screen me. Or maybe she forgot she had a date and made plans with friends. I still don’t know to this day. Either way, I end up having to hang out with this person I had just met and all of her friends. Very awkward to say the least. At one point, one of her friends drunkenly looked at us and yelled, “HOW’S THE DATE GOING????” Needless to say it’s incredibly hard to get to know someone on a first date while you have their friends watching your every move.
We ended up going on a couple more dates (what can I say? Her friends loved me I guess…) but the relationship fizzled pretty quickly. The first date certainly didn’t help.
I’m sure you can top my story. Share your worst first date stories below in the comments. I’ll pick my favorites to spotlight in a future blog post. What happened on your worst first date? Loveawake want to know!
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Alex Wise served over 5 years as relationship expert helping women from around the world figure out the men in their love lives from an honest, male perspective. Alex is one of the contributors and editors for dating website. He is passionate about thought leadership writing, and regularly contributes to various career, social media, public relations, branding, and online dating communities.


  1. I met, who I expected to be a very feminine, woman at a party…we had been flirting on-line and we were surprised we hadn’t met since we knew so many of the same people.
    She looked nothing like her pictures…I said so and she actually said that is why she posted them. Um…really?
    Trying to save the date instead of being distracted by the hot women at the party I suggested we get out of there…try a coffee shop. The quiet and lack of distraction didn’t change that I wasn’t feeling this woman.
    When I told her I wasn’t feeling a connection at the end of the date she was insistant that we did have a great connection and should go out again. I said no thank you and she posted on-line about our great connection that I was running from after our first date.
    Of course our mutual friends asked me about this.

  2. Met a guy on an online dating site. Exchanged emails and a few phone calls and he seemed kinda normal so we planned a date. I took the train in to Penn Station and he met me there, which is were the trouble started. Turns out he’s about 5’3(his profile say 5’11”) and he showed up in ripped (not for fashion reasons) jeans, a ratty Mighty Mouse t-shirt and a stained old sweatshirt. He then told me the restaurant was about 30 blocks away and he wasn’t paying for a cab so I had to walk it in my heels. The “restaurant” was called Curry in a Hurry and was basically the Indian food version of McD’s. During the meal I was reaching for conversation so brought up a movie I had just seen. His response? “I don’t want to talk about that it’s stupid” After silently finishing up as quickly as possible, we left the restaurant and I was going to hail a cab back to the station but he insisted on walking me back. 4 blocks away, he stopped and asked if I knew where I was and when i said I did turned around and walked away from me. Never heard from him again thank God. The worst date ever.

  3. A guy started talking to me on a subway. He knew a lot about film, so of course (I’m so stupid), I gave him my number. He only seemed mildly awkward by then. Then we got drinks and he was SO awkward, and boring, and (which doesn’t help) was wearing A LOT of jewelry even though he was in his 30s. I couldn’t wait for him to finish his drink. At the end he was like “um, call me?”, I smiled and ran.

  4. One of many online experiences, but from years ago. I know better not to go to a guy’s house on the first date now.
    Talked to this guy Mike on the phone, after emailing on yahoo dating for a week or so. Seemed normal. Photos seemed normal too.
    He lived down the street from the Redondo Beach pier, so he thought it would be fun to park at his house and walk down to pier for ice cream. Sounded like a sweet and uncomplicated date to me for a nice Saturday morning.
    Arrived at his house which was nicely manicured out front and a new BMW in the driveway.
    When he opened the door, he wasn’t 5-10″ as he noted, but the same height as I was with heels, about 5-7. He wasn’t muscular and clean shaven either. He had grown a weird pointy goatee, had shaved hair above his now visible pointy ears, had a sunken chest but small beer belly and was wearing shorts with those tennis style socks with balls on the back and leather sandals. He looked just like what I picture a scary leprechaun would be.
    I didn’t want to be rude, so I walked inside at his invitation. From the front door it was a hallway all the way back to the living room and it was lined with rusty metal shelving and old tools on both sides. His living room had dark paneling, one bare light bulb on the ceiling, and had a small tv on a cart with a folding patio chair in front of it.
    Seriously, I got scared at that moment, like OMG, WTF have I walked in to? He was still light hearted and joking but this was surreal. He went into the kitchen and offered me some coffee….I turned toward the kitchen and saw a worn down space with pliers to open the microwave, and paint cans stacked in the corner. He had an ironing board with a stepstool for a kitchen table.
    He could tell I was freaked out because he said..”I bet you’re wondering about my house…yah, it’s not quite done”. He went on to say that his father had passed away and left him this house and left it for him, and he’s been living in it, but was going to remodel it and sell it. I was relieved for a moment, but said, oh, I’m sorry your father passed away recently. He said, “oh, no, it’s ok… he died about ten years ago”.
    I couldn’t take any more, but was afraid to run out, thinking I would trip up at the door lock or something, so I looked at my watch in classic fashion and said, oh no, I totally forgot that I have to go (do something..don’t remember what) but felt like I just needed to get out of there. He was outwardly nice, and felt confused, but said ok, well, i’ll walk you out. We passed by his bedroom on the way to the front door and he said, wait, let me show you my room, and I said…uh, that’s ok, I have to go. He opened the door and from the hallway I could see it was a small room lined with those purple-ish black-light posters of naked women and gargoyles. I said “I gotta go and walked faster…”He said, “come on, lets have sex in my room, it won’t take that long”. I didn’t even respond…At that point, I pulled the front door open, almost broke off the screen door and jogged to my car. He DID call me the next day, asking if I got my stuff done, but I never called him back.
    There have been many more “bad” dates since (i’ve been online dating, what do you expect?) but nothing tops the Leprechaun. Sometimes my friends refer to my “leprechaun date” as their low point of expectation.

  5. […] We’ve all been there…the date where you just missed the cues… She wanted you to kiss her and you shook her hand instead. He wanted to be anywhere but there and you couldn’t stop telling that story about your grandmother’s teacup poodle. When you forget to pay attention to your audience… you run the risk of being “that” date living on your date’s oral tradition of crazy date stories. […]