I don’t normally divulge information about my love life on my blog, because I generally consider it to be too personal and private for open publication, but I had a ridiculous New York dating experience recently that’s just too funny not to share.

D_ is a very attractive Italian-American from New Jersey that I met online. She is a temporary receptionist, although she was unemployed and interviewing for jobs on the day of our date.

We had a few ‘phone conversations, during which I learnt that she was living with her parents after separating from her husband, who had custody of her 8-year old son. She seemed bubbly and fun on the ‘phone, although there were a few “high maintenance” warning signs.

Anyway, we arranged to meet for dinner in the East Village. However, when I emerged from the subway, there were three frantic voicemail messages from her explaining that she’d left a floppy disk with her resume on it at an Internet cafe in midtown, and that I should instead meet her at a Starbucks on Madison and 36th.

When I got to the Starbucks, the staff were cleaning up, and told me that they were closed. I told them that I was there to meet somebody, to which the manageress replied “Oh, are you a friend of D_’s? She’s in the bathroom, you can wait for her.” As I sat down to wait, I could hear her voice shouting from the bathroom –she was having a fairly heated exchange with someone on her mobile ‘phone.

This went on for a while, then it went quiet. I continued to wait, as the Starbucks staff neared the end of their shifts and started wondering aloud what she was doing in there. Eventually I called her on her mobile to ask how much longer she was going to be.

Finally she appeared, smiling and looking very put together but also somewhat flustered, and immediately launched into a story about how she had not been able to go to the gym that night because of the disk fiasco, so instead had taken a Stacker (some kind of extreme weight loss pill) that her hairdresser had given her on an empty stomach, and had then started to feel ill, hence the visit to the bathroom in a Starbucks that was about to close to get changed and compose herself..

As we gathered up all her various bags, she showed me a little fake alligator bag/purse thing that she had bought for herself earlier at a nearby Duane Reade drug store, and once outside she asked if I minded going back to the store to get another one as a gift for the Manageress of the Starbucks who’d been so nice to her. It was about 10pm by now and I was getting pretty hungry, but of course I said “sure, no problem.”

Things were going pretty smoothly as we chatted and walked around the block to the drug store, and we quickly located the little plastic purse — the last one in the store — and a bottle of Jessica Simpson perfume before heading to the check-out.

However, this is where the fun starts: She puts the stuff down on the counter, and then takes two steps back as the cashier rings up the sale. He says “that’ll be $24.99 please.” A long awkward pause ensues. I’m looking at the cashier, who’s looking at me. Then I’m looking at D_, who’s also looking at me. Eventually the penny drops and I ask D_, somewhat incredulously, “Oh, so you want me to pay for this?” to which D_ replies, completely deadpan, “If you wouldn’t mind.”

For a moment or two I’m so confused that I get my wallet out. But then sense returns, I put my wallet away, turn to D_ and say, “actually, I do kind of mind. Why should I pay for this?” She looked a little bewildered for a second, then left the shop, telling the cashier that she’ll come back shortly.

Our exit from the shop is hindered by the fact that, in our haste to leave the awkward situation, we both end up trying to squeeze into the same compartment of a small revolving door, tripping over each other’s feet as we exit. Once we were outside in the street, the dialog went something likes this:

D_: “That was really embarrassing. Why did you do that?”
Me: “I’m very confused by what just happened in there. Why would you expect me to pay for your gift to someone else?”
D_: “It was only $25, if you can’t afford that, you’ve got problems.”
Me: “It’s not that I can’t afford it, it’s the principle. Why should I pick up the tab for your stuff?”
D_: “But you said before that it would be OK!”
Me: “I thought you were asking me if it was OK to come to the store to get the gift before we got dinner, I didn’t realize you were expecting me to pay for it too!”
D_: “You were going to pay for dinner, weren’t you?”
Me: “Yes I was planning to. But to be honest, I don’t think this is going to work out. You’re obviously looking for someone very, very different than me. I think this is the end of the date.”
D_: “Yes, I think so too.
Me: “Well, goodnight.”

With which I turned around and walked away from my first date that failed to last 20 minutes.