My friends and I have experienced some of the craziest dating stories over the years. I have decided to share these comical moments with everyone so that we can all have a laugh at how difficult it is to date in your 30s. Names have been omitted to protect the innocent. I hope you enjoy:
Long Distant Dating
While living abroad I met the most amazing woman. We hung out often and shared great personal conversations. I thought about how wonderful it would be to kiss her, but I always respected the boundaries that she never indicated that I could cross. I returned stateside but never stopped thinking about her. A few months later, she also moved to the States. I lived in NY, and she lived in San Francisco. I was so happy to reconnect after almost a year but when we spoke on the phone or via Skype our vibe didn’t seem the same. Was it my imagination? Why was she being so distant? I invited her to visit me in New York so that we could reconnect. I also decided to pay for her flight to New York. A month prior to her arrival, I hadn’t heard from her. I called, sent text messages and e-mails to no avail. Just when I thought I should call to cancel her flight, I receive a text message saying “Sorry I’ve been MIA; been a busy and hectic mnth. Looking fwd 2 seeing u!” The smiley face at the end of her statement melted away any frustrations that I developed from her absence.
I could barely contain my excitement as I drove to the airport to pick her up. As much as I wanted to share some great conversations with her, I was really looking forward to sleeping with her. A brotha been in a drought in NYC! She arrives. After dropping her bags off at my place we go to dinner. She’s still on west coast time so we have drinks back at my place and talk until 3 in the morning—I’m exhausted. She slips into something more comfortable as we prepare to go to bed—wait her idea of comfortable is a hooded sweatshirt and flannel pajama pants?! That’s okay it doesn’t change my desire for her. It’s time to go to bed. Wait…what?! She’s uncomfortable sleeping in my bed?! Why? She doesn’t really expect me to sleep on the couch? Hold up?! She has a boyfriend?!!! Why didn’t she tell me this a month ago? This is going to be a looooong weekend. Ain’t this a…… Should I tell her to leave now and get a hotel? Nah, I’ll just put her ass on my couch now and tell her to leave in the morning.
Who’s Going to Pay?
My girls and I are sitting at the bar having drinks at the W hotel. A gentleman walks over and offers to buy drinks for us. I coyly accept as I admire his finely tailored suit, monogrammed cufflinks and perfect white teeth. After sharing a few pleasantries, we exchanged cards and he walked away. A few days later while at work, I receive a call from him. He wanted to know if I had time to get a drink or maybe dinner. Once I described my hectic work schedule, he realized he had to act quickly or the opportunity for us to meet may pass. Despite having tons of work, I figured I could meet him briefly at the restaurant around the corner from my office and return to my office afterward to finish up the work I had.
He’s dressed as sharply as he was the first time I met him. The waiter arrives to take our order and I ask for a glass of water. He requests a bottle of wine and orders the sea bass entrée. Who’s he going to drink this bottle with? He did hear me when I said I had to return to work after this? “Are you going to drink a bottle of wine by yourself,” I ask. With a smile he responds, “no, you’re going to join me.” Okay this dude must not have heard what I said. The waiter brings his entrée along with the bottle of wine and two glasses—he proceeds to pour wine into the glass he placed in front of me. I sip it slowly as I listen to this man talk about himself. And talk about himself some more, and even more. Did I really give myself another 3 hours in the office just to listen to this?! The waiter eventually brings the check over. The
gentleman dude acts as if he doesn’t notice it and continues to ramble on. “I’m sorry, but I really have to get back to the office so we should get going,” I said. He says, “okay” but continues to talk. WTF is he deaf?! I reach for my purse and take out my wallet. Maybe this will be the jumpstart to help him realize I really really need to go. He continues to talk. I place my card in the bill. He doesn’t move. The waiter comes by and picks up the bill. Wait….WTF?! I sit there frozen and stunned. Am I being punk’d? He’s going to stop the waiter right? Why am I paying for this dinner!?! The waiter returns and puts the paid bill on the table. Did this dude asshole really just have me pay for his meal!?!!! As I sign the $125 bill in utter bewilderment, I try to make sense of the situation. I leave the restaurant and as I walk back to my office, he steps into his 2014 BMW 7 series.
The following afternoon, my assistant stops by my office with an envelope. In it is a note and a check for $200 saying “thanks for dinner and the company.” I’m never speaking to this asshole again.