My Worst Date Ever

Original art by the amazing Craig Boldman (craigboldman.com)

Willa liked blues dancing, playing her guitar, and had a great sense of humor. Most of our time together thus far had been pleasant. When that early February came around, Willa and I had been together for about two and a half months. We thought it would be nice to take a weekend trip up to New Hampshire and Vermont. We'd visit small towns, maybe stay at a B&B, maybe go on a winter hike, and simply enjoy New England winter. Willa parked her car at where I was living in a Boston suburb and we took off together in my car.

Something you ought to know about Willa was that she had previously told me that she had assaulted a police officer (and had been to court as a result), so perhaps I should have heeded that screamingly stentorian warning bell.

But I didn't!

That first day we stopped at Walden Pond, then drove up to Brattleboro, Vermont. We enjoyed the town, visited a coffee shop, and the local art museum. Then we headed north.

We stayed overnight in a cozy hotel and the next day we planned to explore northern Vermont. We picked out a park and made for it, thinking that it would be fun to go on a hike for as long as we could, then find a little mom 'n pop cafe to warm ourselves by a fire.

My car had plenty of gas and heat, so we made for the park in good spirits. But we couldn't find the park entrance. Up and down the road we drove, but the park entrance simply eluded us. It had to be somewhere, so I kept exploring around the local roads.

As for Willa, she became increasingly agitated. "Where is it?" she asked, "How come we haven't found it, yet?"

Those questions didn't help me find it any faster, so I kept driving. Willa sighed and said, "You know, if I was driving, we would've found it by now. How come we haven't found it? Where is it? This is ridiculous."

I turned to her and said, "You know, you're stressing me out a bit, here. We'll find it."

Then she gave me the iciest stare in the storied, freezing history of icy stares. "I'm 'stressing you out'? Are you–are you fucking serious? I'm stressing you out?"

I replied, "A little, yeah. But I'm sure we'll find the place. We'll–"

"Who the fuck do you think you are? I'm stressing–I'm stressing you out? I'm stressing you out? Who the fuck do you think you are? How dare you fucking say that to me, you fucking piece of shit."

Hmm. Now she was stressing me out a bit more, but I opted to not say anything about that. I just wanted to find the park and hopefully go on our hike and enjoy what I could of my time with the increasingly psychotic basketcase.

She continued, "How dare you fucking say I'm stressing you out. You're a fucking asshole. No wonder you run a bad date site! They're probably all about you! Fucking garbage. Fuck you, asshole. Fuck you."

Surprise! We found the park! I pulled into the parking lot. We were the only car there. I parked and asked Willa, "Would you like to go for a hike?"

She pulled out a book and said, "Fuck you. I'm gonna stay here and read. Fucking asshole. I'm 'stressing you out.' Piece of shit. Go fuck yourself."

Should I turn the car off and allow her to sit in the cold or should I leave it on so she could stay warm? Seeing as leaving it on would require me leaving the key with a psychologically deteriorating nutjob, I opted to turn the car off and take the key with me. I went on a brief hike, maybe 15 minutes tops. It was my hope that when I returned to the car, Willa would have clicked her temper down from 11 to anything less than 11. But that didn't happen. No, indeed. In fact, Willa had clicked it up to 12.

She greeted me with, "Drop me off at a gas station. I don't even want to fucking be with you anymore. I'm fucking stressing you out? We'll fucking see who stresses who out!"

This was Vermont in the middle of the winter. We were three hours north of Massachusetts. There was no way I was leaving her up there. I essentially resolved to drive us back to my place, where her car was, and if she wanted to throw bitter vitriol at me the entire time, I could take it. At this point, I really wanted her out of my car and out of my life.

"Pull over at a gas station. I'm fucking serious. I don't even want to spend one more fucking minute with you. Fucking piece of shit asshole. Who the fuck do you think you are, you piece of fucking shit? Bring me to a gas station, goddamn it. I don't want to spend another minute with you, you fucking disgusting thing."

"Let me just take you back to your car. Then we can just–"

"Fuck you. Drop me off at a fucking gas station right now!"

By this time we were driving through a small town. There was a red light before me so I had to stop. When I did, Willa opened her door, grabbed her bag, and took off down the sidewalk. When the light turned green I pulled over in the first parking spot I found, turned the car off, and searched for her up and down the street.

I didn't find her so I hopped back in my car and called her phone.

Ring. Ring.

On the seat next to me, her phone rang. In her haste to leave, Willa's phone had fallen out of her pocket. I had no way to reach her or find out where she was. I scrolled through her phone contacts, found her father's number (I had met her father before. He was a good guy) and I called him up to explain the situation to him and let him know that I was likely going to have to leave his daughter stuck in the middle of Vermont in the winter with no plausible way to make it home.

"Please, please, please don't leave her there," he implored, "She has to eventually figure out that the only way she's going to get home is with you. Just stay with your car and wait for her to come back and try to get her to see reason. Please."

I liked her father, and he had always been nice to me. He lived a couple of states away so I really was Willa's one and only shot at making it home. I took his advice and waited for her to return.

Sure enough, Willa came back. I asked her, "Will you ride back to Boston with me? We'll just go straight there and I'll bring you to your car–"

"Give me my fucking phone, you fucking piece of shit," was Willa's response.

I gave her her phone and she stormed down to an Amtrak station that was close by. The whole time I tried to introduce some reason into her life. "Willa, please come back down with me. We'll go straight to your car. We won't stop. Let's just go."

"Go fuck yourself," was her reply.

A train came by shortly thereafter and Willa jumped onto it with her bag. She asked the conductor, "Is this train going to Boston?"

The conductor replied, "It's going through Springfield," which is not at all near Boston.

Willa stepped off the train and the train chugged on. She then took out her phone, called a couple of friends, and commanded them to come pick her up in Vermont. From what I could hear, they said, "Why don't you just ride back down to Boston with Jared?" She hung up on them and called her father. "Dad, come pick me up in Vermont."

Her father said, "Jared called to tell me what's going on. You need to stop behaving this way right now and get back in the car with him."

Willa laughed and said, "Jared called you? Of course he did! Of course Jared fucking called you!" she hung up on her father, turned to me, and said, "You need to get the fuck out of here before I call the police and tell them you're stalking me."

At that I returned to my car, called her father and said, "I'm done, here. She's clearly unhinged and I don't really want to be a part of this, anymore."

Her father said, "Please don't leave her up there. I know she can be difficult. But please don't leave her up there. She'll have to eventually figure out that you're her only way out of this situation. Just go somewhere and grab a bite to eat and she'll eventually come around. She'll have to. Please."

Ugh. Again, her dad was a nice guy who had always been hospitable to me. Plus, I knew he was right. I went to a pizza place for an hour and relaxed a bit.

Then, her text came: "All right. You win."

Hooray! I win! I went out to my car and there she was. She said, "I'll ride back with you, but you have to understand that you can't go telling people that they stress you out. That's not cool, and I won't take that sort of shit."

It dawned on me that she was completely remorseless. Indeed, in her mind, I and I alone was apparently to blame for the day's unfortunate festivities. It occurred to me in the same instant that if I wanted to finish things as neatly as possible, it would be necessary for me to placate her and acquiesce completely.

"You're right," I lied, "I'm sorry. It was a stupid thing for me to say in the first place."

She nodded. "Good. Now we can go."

I was pretty sure that if I did anything on the way back to raise her ire even in the slightest, she'd jump out of my car, even if I was going 70 on the highway. Placate, placate, placate. Just get her back to her car and–

She said, "I forgive you for talking to me like that. Even though you tried to ruin our day, I think we should still go for a hike."

I replied, "Nah, that's okay. Let me just bring you back to your car and–"

"I really want to go on a hike."

"No, we really don't–"

"I want to go."


We went southeast and crossed into New Hampshire. We found a snowy mountain and went on a little hike. The whole time, I pretended that everything was okay and that I was truly sorry for the horrible way I had purportedly treated her.

We finally arrived back in Boston and I parked. "Have a safe drive back home," I told her.

She said, "I want to spend the night. I'm exhausted."

Ugh. Fine. We went right to bed and in the morning I walked her to her car. She said, "I'll see you soon, right?"

"Of course you will."

She drove back to her home and I blocked her on Facebook. She likely was quick to realize that I was cutting her out of my life and she wrote me a final email in which she actually apologized for her behavior. That was nice. I didn't respond.

There are those who say I should've left her in Vermont. There are those who say I should've stuck it to her more firmly. To them, I'd say that a life without me is verily the very worst nightmare I can inflict upon anyone.


This is the last story I plan to post on the site (why?). The site will remain up for the foreseeable future and I'll be around to check out any posted comments. If you have a bad date story you'd love to share, feel free to comment on this post and share away (content policy still applies). You can also join this Facebook group to commiserate with me and fellow fans. If you're actually interested, you can keep up with my zany adventures at jaredmgordon.net.

Thank you so much for being a fan of A Bad Case of the Dates! Now and always, I hope you find love and laughter. And hopefully, someday, a good date.



  1. You are a much better person than me Jared. I would've left her in my dust as I sped away.
    Have a Happy New Year!

  2. wow what a bitch. I just can never comprehend why guys put up with it. Hopefully you learned not to be a doormat...btw I think my worst date was worse, at least she didn't start throwing things. Any hoo I really enjoyed reading this site. I remember that I started reading in 2012, and spent hours that first night reading all the archive laughing and crying. My mom had died then and this really cheered me up! Hopefully you'll find love and laughter as well and a good date too. XD :)

  3. Wow. What attracted you in her? Was there signs (hindsight is great) that might have hinted she was unhinged?

    1. We don't have OP on hand often, so got loads of questions!

    2. She was very bright, had a great sense of humor, and was awfully affectionate. We had some good times and lots of laughs. There were ups and downs, but quite honestly I think she had overwhelming anger issues that were just a little too obscured under the surface for me to really see or fully understand at the time. I didn’t leave her in Vermont because I really don’t think she was in her right mind, or was even in full control at the time. Don’t know. But now we all have this delightful story. So there’s that.

    3. You're a gentleman! Good on you for taking care of someone with potentially psychiatric issues.

      I'll miss reading new stories, but since I discovered the site relatively late, I got plenty of reading from archives to keep me happy. All the best in your new project!

      And I'm wondering how Willa is doing now. Perhaps she is reading?

  4. You wrote in a way that made me feel as if I were there! Great job and wow, you handled the stress well.

    I don't have a bad date story but my dad was going through his senior yearbook and he showed us something a classmate of his wrote in the back detailing how she always knew they would be married (despite them never dating) and she was the perfect woman who had it all. My mother and I congratulated my dad on getting the hell away from her after graduation and not ending up on Snapped or Deadly Women.

  5. Ugh - you apologised, went camping AND stayed the night with her after that.

    Doormat. No chance I'd be accepting that. I'd be dropping her at the safest place for her to get home.

    Happy New Year and all the best! Hopefully a Facebook page happens, and someone else can take this site's format and continue the service.

    Great job keeping this place going for so long.

    1. We didn’t go camping. And I prefer to think of myself as someone who doesn’t abandon the clearly sick/those not in their right mind. If I felt physically threatened, that would’ve been a different story. But as it stands, I guessed that this was a manifestation of mental illness or she was otherwise not in full control of her actions, so ensuring her and my safety, in my mind, actually makes me the stronger person. If I’m someday in a nursing home and have a few screws loose and I scream at my nurse, I think I’d ultimately be grateful for the strong human kindness they’d demonstrate by continuing to feed me, rather than abandoning me in some basement. I appreciate your otherwise kind words.

    2. Yeah, you extracted yourself from a situation while optimizing the fuss vs. ethics ratio.

      Thank you from a random stranger for not leaving her in Vermont (especially without her phone).
      And after that, nothing would have been gained by kicking up a lot of fuss yourself.

      A few of your dates you could have conducted yourself differently (IMHO) but this isn't one of them.

  6. Jared, you're a gentleman. She seems to have some serious psychiatric issues and two months before finding out seems to be reasonable. I agree leaving her in the cold, without a phone, would not be an option. Wonder what she is doing now? Is she reading?

    Well, I really enjoyed reading this site and I'll miss reading new stories. But since I discovered the site relatively late, there are plenty of unread stories for me to enjoy!

    As for my bad dates, they're not bad enough to feature here, unfortunately. Or is it fortunately? Once, I had very bad allergic reaction to a girl's cat and left her place with swollen eyes, barely breathing. We did not stay in touch and that's it... Not exactly captivating!

  7. I wonder why you felt as if you had to supervise another adult who wanted to be free of you? It's not your responsibility to call her father, it's not your responsibility to force her to be rational. Honestly your ONLY responsibility at that point was to keep yourself safe. If I was in your position, I would have let her go, and called the police. Instead you were forcing her to accept your judgment and dismissed her's. As irrational as it was, you are not her daddy. I definitely would have left her there, called the state police and explained to them what was happening, and see what advice they gave- not to be disrespectful, but you need to understand that no means no, period...regardless if you disagree with the other adult. People have the right to make bad judgement calls, that's how we all learn. You just enabled her, and at the same time, allowed her to use and abuse you. Also, just because you're embarrassed about this date, sharing it and stating it's the last time you post, sends at least myself a message that you were worried about the replies here. Don't worry, this is your site, and EVERYONE is posting embarrassing stories. You were a doormat in this situation, and sure it's shaming. I myself have been there, along with alot of of us. Keep posting, that's the spirit of your "bad dates" site. Learn a lesson here though, that's the most important thing.

    BTW, I'm getting married in April...guess where we're honeymooning? Yep, Vermont. I think we're heading for Stowe..maybe the Von Trapp family inn. Take care

    1. I’m not embarrassed about this date. Not even in the slightest. Have a good wedding!

    2. Also, this is the last post on the site, period. Was that not even remotely clear?

    3. It was remotely clear, yes.

    4. Usually sites like this are run by mature adults. JMG, you are a drama queen.... You own a forum and have to announce you "won't post here ever again" after writing about a bad date. I won't be back here....

    5. Mistah Jay, do please completely ignore this unreasonable and absolutely bizarre person. We all love you, and this particular brand of bridge troll is not worth your time!:)

    6. https://vignette.wikia.nocookie.net/thehungergames/images/d/de/LEAVE_BRITNEY_ALONE%21_gif.gif/revision/latest?cb=20120421160023

      Leave Jared alone! He's a human!

    7. morrowrd says they won't be back and flounces off immediately after accusing Jared of saying he won't be back and flouncing off. Hilarious.

      The amount of condescension in this comment is staggering. Calling someone a doormat while patting them on the back and saying "there, there, I understand"? Seriously? All because he wouldn't leave an obviously mentally ill woman stranded alone in an unfamiliar location?

      Jesus, get a grip.

  8. Why are so many people calling you a doormat? What the actual hell is wrong with society these days? She went crazy, for sure, and absolutely she doesn't deserve a person so kind and understanding as you, Mistah Jay.

    You were NOT a doormat. She was hours from home, clearly not in her right mind. How would she get home? If she had been kidnapped/murdered/been in an accident or anything else and >I< were in your shoes, I personally would have felt responsible for leaving her behind. Yes, she chose to leave the car, flip out in you, and be an utter bitch, but in my personal opinion that doesn't make it acceptable to abandon her away from home with no other way to return. You played the right card, Mistah Jay. Placate the crazy crazy potentially bipolar or otherwise mentally unwell woman until you know that she is at least safe and then wash your hands of her. Well done. Especially after several months of a good relationship during which I must assume some affection was developed between the two of you.

    I wish you so much luck on your endeavors and just know you won't need it!! Keep it fun, Mistah Jay!

  9. Remorseless? After dumping on you like that? I think the woman shows signs of antisocial personality (sociopathic behavior))

  10. I think it was very noble of you to place her well-being above your pride. It would have been easy to engage in the bickering or abandon her after the outburst. Maintaining composure in a frustrating situation like that requires a lot more maturity and heart. I applaud you for that. You would've been a doormat had you blindly stayed with her after all of the verbal abuse. But, you didn't. So, no, you're not a doormat.

  11. I made a Facebook group called The Bad Date Survivors Group, if anyone would like to join, and keep the snark flowing!

    1. https://www.facebook.com/groups/1775597839413750/

    2. I'm so glad, I was thinking of making one just to stay in touch with all of you lovely people! <3 (Even though you're clearly with Bananas, Steve)

    3. I asked to join the group. I've never commented before, but I've been reading these posts for years.

    4. I just requested to join the group. I was a daily reader and occasional responder.

  12. Thank you for all of the great bad date stories. You will be missed

  13. This story rules lol. I was gonna say...who else thinks we should make A Bad Case of the Dates thread on Reddit?? I read a lot of stories on a thread called Let's Not Meet and its great! But I loved this site, got me thru my work day. Took me about a year or so to read all of them lol. It will be missed.

  14. As a daily reader and occasional responder, I will greatly miss the daily posting. I still love to read the archives and will continue to do so.

    Best of luck on your future endeavors Jared.

  15. "I'd say that a life without me is verily the very worst nightmare I can inflict upon anyone." - I love that line :) It's totally something I would say. Thank you Jared for the many hours I have spent reading the stories you post on here, I was always doing so at work of course. I'm surprised you didn't have more gay dates to post though. Good luck. ~Mark

  16. Jarred did the gentleman thing by making sure Willa got home safely.It wasn't like this was the first date.They were dating for a few months and taking a vacation together so there was time and feelings invested so harder to ditch someone. Also Willa's father was worried about his daughter and that was also taken into account. Women go missing a lot and Jarred would of been a suspect if Willa disappeared.That doesn't make Jarred a door matt. A door matt is someone who constantly lets people take advantage of them. This was a one time situation.


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