YES! Weekly’s ten worst dates of the staff

by the staff

Amy Kingsley

staff writer

My worst date happened on an opening night several years ago when I was still involved in theater. I was seeing a guy I worked with – casually, but the relationship was, to quote astronaut Lisa Nowak, “more than professional.” Unbeknownst to me, he brought a date with him to opening night. That stung, but not as much as his response to my anger when I confronted him later at the after-party, which was to watch the basketball game and try to steer me into a catfight with his date. We didn’t fight, mostly because of the revelation that my second-hand duds and physical well being were worth more than another night with that douchebag.

Rachel Brear

classifieds manager

The reason for my worst date wasn’t anything he did wrong; it was something I did. When I lived in Charlottesville, Va., I met a blue-haired guy who was in medical school. He asked me out for coffee and I agreed. While we were at the coffee shop he started telling me about his life. When he mentioned he didn’t drink and was a virgin, I busted out laughing. Rolling on the floor laughing. I thought he was kidding. He wasn’t. That was our only date.

I went on a blind date with a guy named Chip. We met at a restaurant and asked the normal getting-to-know-you questions. He asked about my first job, and I told him I started out as a receptionist at an investment firm and after a few months I was moved to running the certificate of deposit desk. He asked me how many “hummers” I administered to get the position. Check please! I couldn’t imagine ever getting serious with a guy named Chip anyway.

Kenny Lindsay

graphic designer

I don’t know if this was worse for my date or me. I’d have to say me because she never found out about it and it weighed heavy on my conscience. It was during the after-party of my second prom night that consisted of booze, weed and loud devil music. Things were starting to get hot and heavy for the other couples and I think my date realized she better get out while the gettin’ was good. Needless to say she bailed and I ended up hooking up with her best friend – more than once that night I might add. We somehow managed to make it over to her house where we woke up the next morning and both agreed that the incident would remain our secret (until of course now). You could say it wasn’t a complete loss, but I did feel pretty bad about it later.

Michelle Lanteri

marketing executive

So as luck would have it, when I was 17 I had a serious crush on the “Bagel Boy” as my friends candidly referred to him. I was working at the neighborhood Mailboxes Etc., and it just so happened that he worked next door at the New York Bagel shop (Note: He was a hottie in my eyes). And one night as I was closing the store, he came by to say hello and offered to take me out to dinner the next night. So, the next night – same bat place, same bat time – he walks into the store, dillies around with a little smoke, asks if I’m hungry and insists that we go get some food. We get into his car, and he says, “Let’s go to McDonald’s.”  I don’t really remember much after that.

I had high hopes for this one! My date was tall, outdoorsy and handsome. And I had met him at a rock show at the Cave in Chapel Hill. All things a-go, right? Not so much. Let’s just say that his and my interests did not mesh. He spoke exclusively about assisting children with camping and canoeing, and building his dream cabin (yes, a cabin). And I thought he was this cool rock guy, but it turned out that one of his friends had dragged him to the club that night. So my part of the conversation went something like this: “Oh yeah! … Mmm-hmm…. Really?” Years later we bumped into each other at yet another rock show and I saw him in passing with an ear-to-ear grin, his hand being pulled by his Ms. Right, headed straight for the stage!

Brad McCauley

marketing executive

It wasn’t all that long ago. I went on a blind date, set up by a friend who hangs in low places. That’s where he met her, anyway. The date took place in my house; we ate a pizza and watched a movie. Then we, uh, got more familiar with each other. Afterwards, very soon afterwards, she began talking about getting married. To me. And bearing my children, to boot. I got her out of there fairly quickly, but I’m still trying to shake this woman today. It was not a good date.

Jordan Green

news editor

The only bad dates, as far as I’m concerned, are the ones you pass up. When my mom dragged me across the Midwest to prospect for colleges we visited Earlham, a Quaker liberal arts school in Indiana. A family friend named Malika was a first-year student there. She had long raven hair, a warm smile and a quick, intelligent mind. She gave me a tour of campus and we pushed each other in a swing. Later she invited me to spend the weekend with her at her dad’s farm in Kentucky. I really liked this girl, so I can’t fathom why I didn’t go. To the best of my recollection I had decided that since I didn’t get accepted at Earlham, Malika and I wouldn’t have much of a future together. It sounds lame, and it was.

Again, there is no such thing as a bad first date. It can be just a lark; it doesn’t necessarily portend a lifetime commitment. The same year I was scouting colleges my friend Karen tried to play matchmaker and pair me with a girl, whose name, I believe, was Annessa, for senior prom. Annessa attended high school three counties to the south. She sent me a letter and a mixed tape, noting our mutual reputations for eccentricity. At the time, I was interested in sharpening sub-cultural distinctions, not bridging divides. I was into short, choppy punk songs sung by shrieking female vocalists, preferably from the West Coast, understand? If I recall, Annessa’s mix-tape had a couple quirky songs by They Might Be Giants and some wispy numbers by the likes of Van Morrison. In other words, I squandered my senior prom experience to avoid compromising my refined cultural tastes.

Brian Clarey,


Bad date? Bad date? Man, in the years between 1986 and like 1997 I was Mr. Bad Date, reinforcing nearly every cliché of the total bastard. At high school dances I would ditch my dates to cruise around in the limo with my friends. In college I would show up on dates drunk and later lie about having sex. As an “adult” I would pull no-shows or cut the evening short by saying I had to “get up early” and then go hit the bars. I would break up with women over the phone (this was before e-mail, which really would’ve come in handy back then) or do it in restaurants so they wouldn’t cause scenes (which didn’t always work out like I planned). I would “forget” to bring money. I would head for the bathroom and mysteriously disappear. I would act rudely to their friends. I would flirt with other women. And I always expected sex. Always. All that is behind me now, but I’m guessing it’s too late to avoid that special circle of hell designated for me and my ilk.