(Part 1) It's An Odd Feeling When A Date You Don't Know Cancels

I started online dating again. In the past, I was on Match and, with the exception of a few guys, I met a lot of... characters. None of the men looked like their pictures and two showed up wearing Hawaiian shirts. I try to experience every date like a new adventure, but the guys I met on that site had to be the most lackluster men in L.A. I remember meeting Larry, a real estate insurance claims investigator, at his favorite chain restaurant (this last sentence would have been more than enough warning for any woman not to go). I stared into my glass of bad red wine, trying to visualize where all the exits were located. Maybe during his long pontification, I could sneak out undetected through the side door. But no, I was sentenced to two hours before he took a breath, and I could interject to say my parking meter had surely run out.

I tried eHarmony too and met one very smart, interesting man. My initial impression of Mark was that he was gay. He worked in publishing, looked about 50, was dressed nicely but just seemed to be more effeminate than any straight man should be. He was also the ex-husband of a very wealthy woman, who is a friend of my former boss... which made me feel immediately insecure because she makes 100 times more money than I do. We sat at the bar and talked for two hours and never experienced a pregnant pause. But, it was getting late and, although I enjoyed my time with Mark, I did not have any romantic interest in him, and I suspected he felt the same way toward me. As I thanked him for the drinks and stood up from my barstool, he took particular notice of my footwear and complimented me, "Those are beautiful shoes you have on," he said. I was wearing a pair of Pradas I purchased at the end-of-a-season sale from Neiman Marcus 5 years ago, and realized Mark probably already knew that.

If I never went on another dating site in my life, I could die a happy woman. But I had lunch with a business associate last week who mentioned his son met "a really fantastic girl" on "Millionaire Match". "They've been dating for over a year," he said. I had checked out Millionaire Match in the past but felt artificial trying to find a man based solely on his net worth. However, you don't have to be a millionaire to be on the site and, in order to write about dating, I have to actually go out on a few dates, so I pulled up the website and joined.

The next morning I had multiple emails in my inbox from potential suitors. The first guy I clicked on had put me in his 'favorite' box. He was nice looking, so I read his profile and thought that we had common values and interests. I sent him a brief email. He called me later that night and I immediately liked the sound of his voice, which was kind and soulful. Our conversation lasted for a couple of hours, covering a lot of personal ground. The anonymity of a few photos and a phone provided free license for an open and honest conversation with a total stranger. Closely examining Steve's picture, he told me that he was often referred to as the 'Jewish Richard Gere,' which is ironic since people tell me I look like Julia Roberts because of her big, red curly hair in "Pretty Woman" (and I'm friends with the "Latino Richard Gere"). Steve's a native New Yorker from a prominent family, who now lives in a small town in Northern California-- 374 miles away, according to Millionaire Match.

Other notable emails included a dinner invitation from a 6'6" Yugoslavian man in Santa Monica, WHO TYPED ALL IN CAPS. Six feet, six inches, is really tall. "Oxygen doesn't travel to the brain the same way when you're that tall," noted a male friend. "I'd be careful with that one." A very handsome Italian man in San Diego sent me an email that said, "I don't like name Carolyn, I'm calling Carmela". I thought he was making some obscure reference to "The Sopranos," but no, he just didn't like my name Carolyn and was calling me Carmela. The last email from him that I read said, "Can u make me a star like clooney status???? Lol". (Part 2 continued below...)

(Part 2) It's An Odd Feeling When A Date You Don't Know Cancels

I also received an email from a "75% Italian and 25% Persian" Beverly Hills plastic surgeon, whose specialties are noses and boobs. Danny's profile said he was 40, but he looked more like 50. He emailed me his phone number and wrote "call me". However, my own experience has proven that I have much better luck when a guy is pursuing me, so I emailed him back with my number instead. "How much do you weigh?" he immediately asked. "138," I responded. I weighed myself that morning and knew I was 141, but "130-something" sounds much better than "140-something" so I lied about 3 pounds. "Have you ever had any work done?" "No," I said. I understand the attraction to plastic surgery, however needles, botox and cutting flesh scare me. He directed me to his website to prove he was really a surgeon. There were 'before' and 'after' pictures posted of a nose job and a breast enhancement. I have to admit the new boobs looked really natural. "Would you ever have yours done?" he asked. "I like my breasts," I said, "So, no, I would not 'enhance' them". Was he looking for a date or more clients?

Our superficial conversation carried on for about 15 minutes. He told me that he had only met two women from the site. The first 'woman' he met actually turned out to be a man and the second woman was 200 pounds heavier than the picture she emailed him, which is why I didn't take offense to his pointed questioning. However, since he was being blunt, I also took liberty. "You look older than 40 and you sound tired," "That's because I haven't slept in 9 years," he responded. "Everyone thinks I'm older because most of my friends are doctors in their 60s." He then asked if I drank and what kind of alcohol I prefer. Red wine or vodka are my typical choices. "What about tequila?" "Yeah, tequila's ok," I answered. "We should get along just fine." he said. I didn't feel like I had much in common with Danny, but I didn't know anyone like him and thought dinner could be an interesting and colorful experience. I agreed to meet him later, after his soccer game. "What are you going to wear?" Ballsy question, but clearly he was gunshy from his two prior, shocking experiences. "A black dress and heels," "What length?" he inquired. "To the knee," I replied. "I like black," he stated, "Now it's your turn to ask me questions." I didn't need to. I knew more than enough.

A few hours later, Danny called. We talked for a bit about his soccer game, before he said he was really tired and just wanted to get home, shower and go to bed. He cancelled... After 9 years, he finally wanted to go to sleep. I had rearranged plans to accommodate dinner with him. It was an odd feeling to have a date with someone I didn't even know, cancel on me. He asked if we could reschedule next weekend. "Can't. I have a friend coming into town."

So here I was on a Saturday night, content watching the SAG Awards (I wanted Jeremy Renner to win for THE HURT LOCKER!) when I received an email from Steve that said "... stop looking at all those boys online, you have a date!!!" My 'friend' coming into town next weekend is Steve, the Jewish Richard Gere. He booked a hotel room and a ticket to L.A. Yikes... I hope we have the same chemistry in person that we have on the phone.

"You're Like A Dude With Boobs..."

...said David, "and I mean that as a compliment." I was in Salt Lake City with David, Kyle and Bob. We had just wrapped a shoot and were eating and drinking at an Italian restaurant, before catching our plane back to Los Angeles. I accepted what David said as a compliment, but then wondered ultimately if I had lost my femininity around men. I grew up with three brothers, I work in a male-dominated industry, my friends are mostly men, and I enjoy the company of men. I'm around men 24/7, yet I'm single and date infrequently. Have I become too much like one of the guys that men aren't interested in me as a woman anymore?

"If I keep eating this way, I'm going to look like a dude with boobs," exclaimed Bob. I laughed as I contemplated my predicament.

My insecurities rose to the surface. Do I need to be more feminine? Should I change my wardrobe? Let's face it, working in independent film and on nonprofit videos, doesn't leave me with much discretionary income for clothing. Teenagers in Los Angeles have a better wardrobe than I do. Maybe I need to dress sexier. Hmm.

Yesterday, I met Tom Ford at the Spirit Awards brunch. I introduced myself and told him our movies were nominated in the same category. I was quite taken by how exceptionally polished and handsome he is up close. Most celebrities look quite different in person, but Tom Ford, wearing his signature sunglasses, could have walked right out of a color, glossy, high-fashion magazine ad. Not a whisker was out of place. He's undeniably handsome and has a movie star look. (I predict Tom Ford will be starring in his own next film). A photographer approached us, asking to take our picture, so we turned and I placed my hand on the back of his 'Tom Ford' jacket. "Oooh, cashmere" I cooed. "This is the most casual outfit I have," he said. "Really?" I said, "This is the most dressed up I get." "No, I do have jeans," he corrected before he graciously exited. I began to assess my own outfit: my favorite J Brand jeans, Zara jacket, Hugo Boss white-collared shirt and Charles David shoes. Oh god, did I really just introduce myself to Tom Ford looking like this? I quickly reassessed the room of independent filmmakers and took solace in the fact that ok, I think I fit in just fine with everyone else.

Slightly frantic however, I called my brother Leo and asked him if he thought it was bad to be called 'a dude with boobs'. "Well, I don't think it's good," he said, "Objectively speaking, you're pretty and sexy so that's not an issue. But you 'don't suffer fools gladly' and men don't want someone to call them on their bullshit." He's right, I thought. And working in the entertainment industry for the past 20 years, certainly hasn't made me any softer. I contemplated a past relationship. My biggest problem with Kent was that he never dealt with any of his own personal issues. He literally and figuratively swept everything under the rug. It was hard for me to respect a man who wasted opportunities to learn and grow. But, at the very least, I knew after speaking with my brother, that my problem wasn't with my wardrobe.

"Men like that moment of surrender,'' said Ivan, a friend of mine for ages, "That's what it's all about, that moment when the woman surrenders to you". I understood immediately. I know the moment he described and any woman who has ever read a romance novel knows that moment too. Many women's fantasy is to be seduced and eventually succumb to their ideal man. I am no different. But, how could I ever 'succumb' and be 'conquered' if I was considered to be one of the guys?

I did not know where to turn for an answer so I decided to call David and ask him to explain exactly what he meant. "You are very comfortable hanging out with men and can laugh at the same stupid things guys laugh at without acting superior like some women do, especially when it gets really raunchy." Ok, but I asked him if I lost my femininity in the process? "No, Carolyn, besides having red hair, you're a ball of fire," he stated, "You're smart, in touch with your emotions, honest, tall, have long arms..." My confidence was coming back (but is having long arms a good thing? "...but men are fearful of these things and because you are powerful, I think you scare guys off." Oof. I have heard this before... many times. I was sinking back into insecurity. But what do I do? If I had the answer, I wouldn't be writing about my experiences looking for a meaningful relationship in Los Angeles. But what I do know is my life would be a lot less rich if I didn't know all the men who are in my life-- including David who has an amazing wife and kids, is very close to his mother, easy to talk with and completely comfortable around women. As a matter of fact, I thought, David, you're just like a "chick with a penis."