The Misadventures of Dating in Your 30s Part I

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.


12 Responses to “The Misadventures of Dating in Your 30s Part I”

  1. The Janitor Says:

    Funny post. Been in both of these situations before.

    The weekend visitor situation is the most awkward though because you are pretty much forced to have this person in your home for 2 or 3 days AFTER you find out what should have been disclosed to you (the fact that they have a significant other) BEFORE they accepted your invitation to stay at your place. If the woman/man knows that they have a significant other then why are they accepting invitations to fly across the country to spend the weekend in somebody else’s home?

    Re the other situation, I went out with a young lady once who literally talked about herself for the entire evening. At some point, most people will realize this and say “so enough about me, what about YOU?” That never happened. She was more than happy to talk about her Ivy league education, her trips around the world, her sorority, etc. Which, by the way, all of these things are great. I certainly did not begrudge her experiences. But at no point during our entire conversation did she ever stop to ask me any questions about myself. Which normally means that a person is just not that into you…but here’s the kicker: after our date she blew up my cell over the following weeks with several messages wanting to get together again. No thanks.


    • LIST Says:

      Haha I’ve learned the hard way to stay clear of those who talk about themselves and rarely ask you how you’re doing! Since I know you’ve finally found “the one” we can look back at those experiences and have a nice chuckle. Thanks for sharing!


    • LIST Says:

      Next time we need to bring that very lively comment to this comment section. I was too busy during the day to keep up. One minute there were 12 comments next there were 98. But thanks for the riveting dialogue and the interesting perspectives from all parties. 🙂


  2. sohimor Says:

    Not a bad post, would be interesting to hear the correlations and lessons learned from previous experiences. These dating stories (at least the ones about you) seem similar to the tale of Sisyphus. Anyway, good luck with your future dating endeavors and keep them coming.


  3. LIST Says:

    The lessons and correlation would take a few blog posts of their own. And since I have a hard time maintaining this blog as it is, that would be too time consuming. But at the end of every bad experience is always a lesson and a good laugh. As for Sisyphus, I beelive he was a liar so I’m not sure of the correlation. Also, don’t you owe me a phone call/e-mail sir?


    • sohimor Says:

      The reference to Sisyphus was about his punishment. In any case, I called you and left you a VM and emailed you about setting up a time to discuss next steps. I wasn’t sure if it fell through the cracks or what and I thought it best to let it go. I’ll give you a call this evening.


  4. undercontract Says:

    *sigh* the woes of dating in our 30’s…great post!


  5. Anonymous Says:

    These situations are both so unfortunate. While we are more connected than ever with our smartphones/ghat/twitter/Facebook, I wonder if somehow we are losing our ability to actually communicate effectively? On the other hand, if some lies through omission or commission then that is out of your control…and that can happen at any age 🙂


    • LIST Says:

      Your point is well taken in that our increased modes of communication has in some ways impaired our ability to communicate effectively. Touché to your point about having these experiences at any age. Hopefully I won’t be blogging about my friends and I and our dating woes at 50! 🙂 Thanks for sharing your thoughts.


  6. Anonymous Says:

    what role do we play in these situations; were there signs? Did her absence show her lack of interest or time she was spending with her man, and sometimes do we hold on for personal gains, a dry season for example. how often do we meet the representative or even imagine people to be someone we nor they are not ? dating truths, we often lie to ourselves and arent reflective..what happens if he sees the real me before i am ready..


    • LIST Says:

      These are all great questions and considerations that I may explore in a later post. My intent in writing these dating chronicles was not to dissect who is right and where things went wrong. It was merely to find the humor in a situation that wasn’t so funny to the person at the time. But to respond to your inquiry, sometimes we believe what we tell ourselves rather than asking questions to reach the truth. And he did say that he had “been on a drought in NYC.” I don’t believe that people in their 30s should have a representative or hide who they truly are (although we are forever a work-in-progress), but I think we often romanticize what we want a situation to be rather than communicating with the other person to find out what it really is; and perhaps this was the case in the first scenario. Thanks for sharing your thoughts.


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