Last summer, my friend T asked me out on a date. We had slept together six months previously, and though it had been awkward I wanted to give him another chance. He asked me to meet him at the metro station near my house, saying he had “the whole date planned out,” but refusing to tell me what it was. I showed up in jeans, a tank top, and my new flower-print heels.

I asked him what we were doing, and he said we were going to the movies. While we waited in line for the movie (the sixth Harry Potter, which he picked without asking my opinion), he passed time by insulting my shoes, my hair, and my outfit. By the time we entered the theater, I was offended but decided to try to relax and enjoy the movie. The theater was packed, we were surrounded on all sides by families, including many kids.

Everything was going fine, until about 30 minutes into the movie when he grabbed my hand very suddenly and nervously. I thought he was trying to hold hands, but instead he shoved my hand down his pants! I wasn’t sure if it was Ron and Hermione that did it or me, but he was already quite excited. I pulled my hand away quickly, and started laughing. He scooted away from me and glared, continuing to glare for the next 20 minutes.

Then, his cell phone rang. He ran out of the theater, and came back five minutes later saying that his mom had called and he needed to go home, but I was free to stay and enjoy the movie (which was in a dodgy part of town and wouldn’t end until late at night). I said that I’d leave with him instead.

He refused to take the train back into the center of town, instead saying we’d split a cab and I’d get out first at my apartment. As we neared my place, he confessed that he had no cash and I’d have to pay for the whole taxi (including the 30 minute ride from my place to his). I threw some cash at him, disgusted, and went home. Awful!

I work as a waitress at a dive bar, and in the course of my employment I tend to get hit on a lot. As a rule, I don’t take any of these (usually drunk) guys up on their offers.

However, last summer a guy came in who seemed pretty cool. We struck up a conversation, and when he asked me for my number I figured, why not? He seemed to have a lot of nice qualities – he said he was an English teacher, he played the guitar, he was the same age as me, and he was new in town (hence at the bar alone).

The following weekend, we met up at a bar in my neighborhood for drinks. Unfortunately, though I was in my date-night best, he looked like he had just come in from doing yard work – grubby t-shirt, ratty shorts, flip-flops. I decided to let it slide, and we got to chatting. After a few drinks, he didn’t seem so bad so I agreed to a second date.

For the second date, we met at a bar/restaurant in his neighborhood for dinner. When it came time to order, he said he wasn’t eating because he didn’t have any cash. Finally, he agreed to get something when I offered to pay (it was dinnertime and I was hungry). As the evening wore on, I came to find out that he was not, in fact, an English teacher. He had interviewed once for an adjunct professor position but was actually an unemployed subcontractor. Though I was having some major reservations at that point, I agreed to go hang out at his place for a little bit after dinner.

When we got there, he told me that his electricity had been shut off for non-payment. As such, it was pitch dark and hotter than hell in there (it was July in the city). I beat feet out of there, and stopped returning his calls, at which time he started sending the craziest texts- first obscene, then angry, then begging. Eventually he got the message and stopped texting when I never responded.

After that, I never deviated from my no-dating-guys-from-the-bar rule.

Back in my college days, I agreed to go on a date with the friend of my very sweet next door neighbor Tom. His friend was kinda cute and had a bit of the bad boy look to him and we agreed to a double date. The four of us made the 45-minute drive to the city to see a free movie at a popular historical site. I had wanted to see this movie for a while, but I was not happy with my date’s behavior: walking on the seats at the 100-year old theater, loud complaining and inappropriate laughing, which eventually forced an usher to come and ask him to please quiet down. After the movie, we worked our way downstairs where there was a wedding reception going on.  Since parking is an issue downtown, we had parked across the street at a mall. This wedding reception offered free validation to its guests. So while the three of us stood there mortified, my date crashed the reception, grabbing some food and a validation pass on the way.

As we were making our way to car, we passed a sporting goods store and my date said he needed to pick up a bike part. Being pretty annoyed with him by now, I opted to wait at the front of the store. About 10 minutes later, he came back saying they were out of the part he needed so we went to the car. I was ready to go home, but the other couple wanted to go to dinner at a local pizza joint. On the way there, my date noted that he only had $20 for dinner, saying, “So you can’t order a drink and we’re gonna have to share.” I told him I’d pay for myself and he acted all pissed, like I was hurting his manhood. As he pulled out his wallet to pay, he also revealed a small bike part still in its packaging. Yup, that’s right. He had stolen it. On a date. This knowledge and confrontation of the theft led to a very awkward and silent 45-minute drive home. At my door, he grabbed me and kissed me, sticking his tongue down my throat. Resisting the urge to vomit, I wordlessly opened the door and slammed it.

He called a few times after, but I never returned them. A few weeks later, my roommate had to watch court proceedings for her criminal justice class. She watched his trial for stealing $400 worth of CD’s from Kmart. Needless to say, I never saw him again.

After a few drinks with a co-worker at a pizza joint and numerous games of pool, I decided to give my number to a guy we were playing against. I’ll call him “Steve.” I’d just broken up with someone and wanted to make my first foray back into the dating world. 

The next day he called me up to gush about how much fun he had and how he was excited to take me out. We made plans to go for dinner later in the week. He left it up to me to pick the place. I asked if he liked ethnic food and after being assured that he did, I chose a little Thai place with great reviews.

We decided to meet and take the bus together to the restaurant. Steve didn’t drive. It was -25F. I grabbed a cab and told Steve to jump in at our designated meeting place. He made a feeble attempt to pay for it when we got to the restaurant. Needless to say, I was the one shelled out the cash. 

After we took our seats, the waiter asked if we would like drinks. As I scanned the wine list, Steve said “Uh, uh well water’s fine with ME.” I was peeved and felt like I had to get water too. Steve then went over the prices on the menu and told me he really wasn’t “that hungry.” He also didn’t like anything too spicy, which was tough since we were in a Thai restaurant. 

When the bill came (no coffee or dessert), it sat there for 20 minutes until I picked it up and asked if he’d like to split it. He jumped on the offer stating: “Yah, yah, if that’s what you wanna do!” I paid my half AND left the tip.

I called two cabs and made an excuse that I had other plans nearby. We walked out and a cab pulled up and Steve jumped in. I was left standing downtown in the freezing weather alone. When I didn’t return his texts or calls after that lovely evening, Steve got mad and texted that I “was no prize anyways.”

Catching a cab in New York City often requires a very specific set of combat skills. Curbside battles for taxis are not uncommon, as are aggressive pedestrian advances up or down one-way blocks to flag a ride before rivals stationed on street corners.

We’ve also had two Very Worst Dates featuring NYC taxis (the Union Square to the Lower East Side hop and the downtown Manhattan to Williamsburg version). So when we heard of a plan to encourage the metropolis’ denizens to share cabs during peak hours last week, we only considered the dollar-saving sense of the move. It turns out there might be an upside for the love life of New Yorkers as this letter to The New York Times from a man (and stand-up comedian), who’s twice dated women he met after sharing cabs with them, suggests. 

So if you are single-and-looking in the city (and the near-bridge parts of the outer boroughs), survey your surroundings for fellow flaggers. He or she might be a potential date. Think of it as another gift of the recession. Even if it does not work out, at least you’ve saved a few bucks. And there’s always the next journey…

Our current Great Recession is getting tougher every day. Could dating, em, rich be the way out? We went to Tatiana Boncompagni, a journalist and author who’s specialized in chronicling the ways of the rich and aspiring, for advice on following the money. While researching her second novel, Hedge Fund Wives, she took a lot of HFWs to lunch and asked them all sorts of prying questions, including how to successfully date (even in this economy!) a hedge funder/banker/financier for that Happily-Ever-Harry-Winston-after.

Here’s what Tatiana, who’s happily married, gleaned tips-wise: 

1. Pretend not to care about money, but look like you’ve got plenty of it. (No matter how bad things get, he still doesn’t want to date a girl with chipped nails, frizzy hair and overgrown eyebrows.)

2. Cook for him. (Broiling a steak is surprisingly easy, ladies.)

3. If you happen to make more money than him, don’t rub it in his face. (And don’t tell your friends, who will gladly do it for you.)

4. Try not to laugh when he starts crying at the ATM.

5. Knowing how to give a great blow job works in any economy.

And Tatiana had a few more words of wisdom to add to this list: 

“If you follow these simple rules you may just be able to survive the recession with your relationship intact. But might I suggest that any of you eager readers out there take a second or two to ask yourself: Is it really worth it? Consider the opportunity costs—i.e. the hotties you could be dating—and the costs (all the upkeep and ego stroking!) versus benefits (that diamond engagement ring is getting smaller by the day…) and come to your own conclusion.”

After a dry spell, I decided to accept a date from a guy I met online. He looked normal on paper: was around the same age as me, was an elementary school teacher and we had similar interests. I was a bit wary about his passion for cycling as from previous dating experience had found cyclists to be a bit arrogant and self centered, but I didn’t want to paint all with the same brush. Although he asked me out on the date, he wanted me to organize it because he “was teaching and just didn’t have time.” His tone was that he was teaching the leaders of the future, but in reality he was a Physical Education teacher to nine year-olds. He wanted to try Latin dancing so I decided on a style I liked because I had always wanted to learn it. He also told me that he doesn’t like to call dates “dates,” but he calls them “catch ups” because they could elude to “something more when called dates.” 

The lesson was at 8pm so I suggested dinner prior, but he advised that he would be eating something from home. I met him after work at a little cafe where I ate dinner and listened to a one-sided conversation about his life, which confirmed my thought of cyclists. I enjoyed the dance lessons, but he seemed to struggle a bit with the steps. Near the end he said he was having a lot of fun on our date (I thought he didn’t call them dates). At the end of the night I thanked him for the evening and I advised him I was catching a cab home as it was 9.30pm and we were in not the nicest neighborhood. His car was nearby and I lived on his way home, but he didn’t offer to give me a ride. Just after he left I received a text from him saying that he “had a nice time but didn’t feel a spark so thought it best we be friends.” Bless him for his honesty, but he confirmed his asshatness thinking that I was more into him and saw more.

Funny thing is, I signed up for private lessons and wrote about how excited I was about this on Facebook and received a slightly angry text from him saying that I obviously enjoyed the lesson more than I enjoyed the dancing partner. Spot on.

This Chris Isaak look-alike who I met out one night Downtown invited me to lunch on his work break near Central Park for our first date. So I walked about 30 blocks because it was a nice day and I was trying to find ways of saving a buck. I met him at his workplace and he said he had to stop at the ATM where he took out $40. He asked me if I had ever had a hot dog in Central Park; I hadn’t so he said he was going to take me there. I thought it was cute and a fun thing to do so I agreed. We found a stand and he went up and ordered two hot dogs, but only one drink. He then proceeded to put on a bunch of toppings on both hot dogs and started eating one of the dogs. Then he asked for his drink that I was holding and stated, “I’ll meet you over there at that rock.” He bought himself two dogs and a drink, as I stood behind him, and proceeded to eat his in front of me without a clue that he was the one who asked me to lunch. And how much could a hot dog cost? He thought nothing of it, but I didn’t go out with him again. I wish I would have said something on the date or confronted him about right there on the spot!

When I lived in New York City, I actively dated on Match.com. My Very Worst Date happened when I met a guy at a Union Square restaurant. I walked in and saw a guy sitting at a table looking around, but he was clearly 10 years older than the photo he’d posted online. His hair was also much thinner, but I decided to give it a shot anyway and introduced myself.  The waitress came right over and asked if we would like anything to drink.

“No, we don’t want any cocktails,” he said rather curtly.

I let it slide because I thought he might be an alcoholic for a second. Still I was annoyed that he spoke for me.

“Well, can I order a soda then?” I asked.

“Do you have to?”

I was turned off by his cheapskate ways but I still tried to enjoy the rest of the meal since he seemed fairly charming otherwise. After dinner, we stepped out of the restaurant into a rainy, rainy night. Since we were both headed to the Lower East Side, I suggested we share a taxi.

“Do you have your Metrocard with you?” he asked. “Because we’re taking the bus.”

I had one in my back pocket, but I was shocked that in the cold rain he would want to wait for a bus just to save a couple of bucks.

“And is it one of the unlimited ones because I forgot mine?” he added.

I gave him the card, which had four bucks left on it, and I hopped in a cab to meet my girlfriends.

It turned out to be a total bust. My boy sat there not clapping, not singing (who doesn’t know the words to Hard to Say to I’m Sorry?) and definitely not moving, never mind swaying or dancing.

On the way home, he told me he wanted to grab food and drove up to a Burger King drive-thru. At this point, I was shocked to silence. He ordered his food and then casually asked me if I was hungry. I told him I was “fine.” After getting his meal, he drove to his house, got out of the car and made his way inside. I had no choice but to follow him.

He finally wolfed down the Whopper and fries and offered to take me home if I wanted him to. Um yeah! At my front door, he asked me if I wanted to go out again next weekend. I told him no, I didn’t want to ever go out with him again.

I heard through the grapevine that he’s now married. I wonder how often he and the wife eat at Burger King…