Tag Archives: bad dates

Dealbreaker: Drunk On A First Date

I should have known better than to meet handsome Dan at one of the seediest bars in Brooklyn, but looking into those baby blues that were a good four or five inches above mine, I couldn’t help but feel weak in the knees. He took my number and after a few texts we decided on getting drinks the following weekend.

I was two blocks away at 8:30, the time we had decided to meet. My phone rang. “Hey, where are you?” he asked. This being our first voice-on-voice interaction, I didn’t think anything was amiss. Maybe he was just a teensy bit nervous. Keep reading »

Dealbreaker: The Checkbook Balancer

I was in my early 20s, living in New York City and barely scraping by. Even though I was making ends meet by some combination of waiting tables/temping/focus groups, I still always had enough money to pay my rent and indulge in highly caloric, fruity martinis. Before I was on my own, my father instilled in me the importance of monitoring my money so I never overdrafted my measly bank account or bounced one of those fairy checks I was so excited to order. Keep reading »

Dealbreaker: The “Rate Me” Guy

The first fire-red flag with Jack should have come across loud and clear when he asked me — in our very first email exchange – to “rate” his online dating profile picture. This is Match.com, I thought, not one of those sort-of-creepy hot-or-not sites. I wanted a guy to take me out for dinner, a beer, maybe even have a little make-out action; I didn’t want to be a judge on an episode of “America’s Next Top Model: Males of Match.com Edition.” Keep reading »

Dealbreaker: He Told Me to Lose Weight

Dan had a big grin in his profile picture, like he’d just said something super funny. He liked foreign novels, old buildings, and could spell in complete words. He looked like a cute professor.

Could this be … my guy?

I’d been online dating for a few months – long enough. There were the guys who lied about their age/height/marital status, the guy who said I was a dead ringer for his favorite blond sports reporter and would I mind putting on a fake newscast for him, and my favorite, the guy who asked me not to use face cream because he had a phobia about moisturizers. Keep reading »

What Was Your Worst Dating Experience?

I’m newly single and definitely on the dating scene. I’ve dated a couple of guys here and there. Cute, not so cute, smart, not so smart, I consider men to be like ice cream flavors; you can’t judge until you’ve tried them. Well, this one wasn’t really worth trying. If I compared this date to ice cream, it would taste like old rotten milk with sprinkles and a Yarmulke on top. He asked me on a date and also asked that I pick the place. I picked a place that was fairly priced and conveniently located. Not only did he show up 10 minutes late, he showed up wearing a blue cotton button down collared shirt, tucked into light denim washed skinny, but not so skinny, jeans. They were a cross between skinny jeans and boot cut, quite frankly, I’m not sure what they really were. He had on a brown belt, and these awful black leather, scuffed, square toe loafers. I was already turned off. Call me super shallow but this outfit was too much to digest and we hadn’t even started dinner yet. We talked about life and what not and when the bill came, I put my hand on it and simply asked if I could split it with him. I’m not one to expect a man to pay for dinner, especially on a first day, but instead of simply answering with a “Yes, sure” like a gentleman would have, he responded by saying, “Yea, I was hoping you’d say that, I can’t afford to pay for a dinner for two people right now.” He then pulled out his headband and put it on his head to hold his hair back. I was so confused as to what was going on at the table. This date was a date from hell. I ended up paying for more of the bill than he did and I guess it was better off that way. I paid to not go on a second date.

This date was surely from hell, and beyond uncomfortable … do you have any terrible dating stories to share? Keep reading »

Would You Hire An Online Dating Assistant?

In the world of online dating, it’s a tale as old as time: You meet somebody online who’s funny. Genuine. Charming. Until the IRL date happens … and you find out that he’s not quite the person you found yourself engaging in witty banter with on the Internet.

Virtual dating assistants exist exactly for that reason — to give those (primarily guys) who lack the capacity to reel in a potential date a little help in the profile-creation department. Read more Keep reading »

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