Welcome to Hollywood. What's your Dream?

Since I usually travel quite a bit for a living, I am on planes all the time. Whether I talk to the person next to me or not really depends on what I have to do on the flight.

This trip, I was flying from LA to Chicago so I knew it was going to be a long one. We were on one of the big planes and this guy sits down next to me with a ton of energy. He introduces himself and proceeds to tell me he is going to give a speech at a convention and is nervous about his presentation.

He then asks me if he could give the presentation to me? Sure, I am game. He starts his presentation and I said wait, stop right there, I am bored already. You need to start with something to break the ice. I learned he is from New Zealand as I could tell with his heavy accent. I told him he needed to say he is from New York or something to that effect to get a chuckle.

Anyway, we re-write his entire presentation. He is feeling good about it. I learn in the span of a 4-hour trip that he is divorced, has two kids and his ex- wife cheated on him. Not just a regular cheating kind of thing, the entire town knew but him. I kind of felt sorry for him.

We chatted the whole time until Seinfeld came on our TV's, we both grabbed our headphones at the same time. We were totally cracking up at that show even though we had each seen it 1,000 times. It was all very comfortable.

I also learn that he is 16 years older than me. As our flight was ending, he asked me if he could have my number? I thought sure, why not. He was fascinating.

Since he lived in Santa Barbara and I lived in Chicago, it made things a bit tricky to see each other. However, at the time, I was in the West Coast quite a bit for work so I would always make a point to see him.

He was very serious and really wanted a relationship. I wasn’t serious and just liked hanging out with him. I tell you, they grow ‘em chivalrous down in New Zealand. He was always sending flowers, cards and checking in.

One night when I was in LA, he wanted to take me to Geoffrey’s in Malibu. If you aren’t familiar, it is a great restaurant where many celebrities go. We were running a bit late and when we got there, he immediately greased the hostess with a fistfull of cash to be placed at the nicest table in the restaurant overlooking the water.

There were many great nights like that. However, I could never get over his lifestyle. LA and Santa Barbara felt like a fantasy to this MidWestern girl. I saw his house on the ocean and thought, people don’t really live like this?

Because I was somewhat indifferent towards him, he was always looking for some reassurance from me. He used to ask a question that always caused me to roll my eyes. When we would be walking, he would want to know if we are walking at a good pace? He would ask that silly of a question just to get me to say yes. It came across as needy to me and I struggle with needy. I did understand his concern though because my poker face was strong.

He had quite a bit of money from the recording business so no expenses were ever spared. He would always tell me he will pay for my flight and I would say I can pay for my own flight. That answer surprised him because he is not used to someone not taking him up on it.

I could see how people can get caught up in this scene but, it is just not something I could do long term. I realized this wasn't really fair to him. He was developing feelings, and I just wanted to shop with him on Rodeo Drive like Pretty Woman.

The definite deal breaker appeared eventually. When we would be out to dinner, he would ask me to sign the check. It was his credit card so he would always instruct me to tip 30% and sign his name. This was because he couldn’t see the receipt very well. As someone who was in my early 30’s, it always made me feel like I was out with my parents. I could never get over that.

So, eventually we went our separate ways. I did enjoy spending time with him but realized it really wasn’t fair to him. His feelings were a bit stronger so it was best to let him go.

Lesson learned? Every girl should be spoiled by a Sugar Daddy for a little while at least! And remember, the window of being someone’s partner verses being someone’s caretaker can be slim with a big age difference. I was definitely not up for that task at the time.