The Millionaire's Grandson

Submitted by Anonymous

When I was twenty years old, I met an attractive silver fox in his sixties or seventies. He kindly said hello to me in the lunch counter line near my office's building campus, and gave me a cute old man wink. He was dressed to the nines in a gray suit, expensive leather shoes, and a watch that looked like a small fortune. He was polite, gentlemanly, and his speech sounded like he was very well-educated. We small-talked while we waited in line and then parted ways to eat our lunches. 

A little while later, I was heading out to my car in the parking lot, and I heard his voice again. 

"Excuse me, miss?" I turned around and he looked eager to talk to me again. "This is going to sound very strange, but... are you single?"

'Oh god', I thought to myself, 'is he asking me out? He's almost as old as my grandpa.' I hesitated to respond.

"Sorry, that came out wrong. I'm not asking for me. I have a grandson who I think would find you attractive and interesting, and I'm wondering if I could get your number for him?"

I hesitated again, and he proceeded to tell me that his grandson is an obviously attractive and wealthy salesman, drives a Mercedes, and is very on track with his goal to be a multi-millionaire by age twenty-five.  

Against my better judgment, I gave him my number, and headed back to my office. I figured I wouldn't hear from the guy, because why would a guy with all that going for him need a setup from  his dear old grandpa?

Within two days, he had called me, and date plans were set.  His grandpa hadn't lied. He was tall, dark, handsome, well-dressed and smelled fantastic. After picking me up, we walked out of my apartment building, and I headed toward a nice black car parked nearby. 

"Oh uh... my ride's over here." he said while he motioned toward a Vespa with two helmets. I should mention that it was November, and dark out, with a wind chill that felt like it was 20 degrees colder than the already freezing night air. "Sorry, I should've warned you that I didn't bring my car. Hop on, the restaurant's not that far away." 

I didn't quite know how to avoid awkward situations with men at this point in my life, so I put the helmet on, hopped on the back of the Vespa, and we sped through the freezing night air. By the time we got to the restaurant, my nose was running, my hair was all messed up, and my mascara was beginning to run down my face. I was freezing and pissed off. 

Dinner started nice, we had great conversation flow, and he seemed like a cool guy. Then, the conversation turned to his grandpa getting him a date, and he ended up explaining that he was just a few weeks out of his divorce. It could've stopped there, and been fine. That's a perfectly ok piece of information to drop on a date. So, he might have a little baggage, no big deal. 

But, he talked for over an hour about all the ins and outs of the divorce, and his marriage, and how deeply in love he still was with her, but she wouldn't love him no matter how much he asked her to. He called her crazy, heartless, and even threw in the word 'bitch'. He explained all her cute little personality nuances, how my outfit reminded him of her, and how he just wasn't ready to even be dating. He also mentioned that she had borrowed his Mercedes. Oh, and during part of the conversation, he actually teared up and I had to pretend it was fine, because I felt like I had no choice in the matter. 

It wasn't fine. It was so completely awkward.

You can go ahead and guess how awesome that ride home on the back of his Vespa was, and how fun it was when he walked me to my door, and still tried to get a goodnight kiss which I skillfully avoided.

He never called me again, and I wasn't disappointed. Bye bye, sad rich guy. I hope you were able to move on and get over your heartless ex. 

Note to self: When a grandpa asks you out for his grandson, maybe ask if he's freshly divorced. Or, if he picks you up on a Vespa in the winter, maybe don't get on it.