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Thursday, 18 March 2010 10:44

Ellen Krug, Inside Out: Reflections on 100 Dates

Written by Ellen Krug
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Ellen Krug
Ellen Krug is a writer, lawyer, human. She was a trial attorney for 28 years before realizing there is more to life. She is now on sabbatical to write a book, and if that does not work out, to wait tables. She is parent to two adult children and hoping for the best, despite the odds.

Since coming out as transgendered, one of the things people say to me goes like this: “Oh, you must feel like a teenager again, starting all over with a new life.” I have to admit that some of this is true: I do feel like a teenager again (even to the point of taking acne medicine), but this is not necessarily a good thing. One of the negatives is that I’m learning things all over. Like dating. Like being alone. Like wondering if I’m cute enough to attract someone other than the guy left after last call.

I’ve probably gone on 100 dates of one sort or another since 2004. And just to be sure that all of my bases are covered, I have dated both men and women. One would think that this “doubles my chances” for a happy relationship. In reality, it just means more chances for me to meet people who absolutely will not provide me with a happy relationship. I can report that I’ve not disappointed myself in that regard. I had never thought finding a quality, durable relationship would be so difficult. Of course, maybe it’s just me, Princess Ellen.

So as a 53 year old teenager, let me report on some lessons learned on the 21st century dating front.

 

My first post-marriage date was with a bisexual woman who posted an attractive picture on Match.com. She was extremely witty in her on-line profile and it made me think, “I’ve got to meet this person.” We set up a meeting at a restaurant. I walked into the place and the host pointed to a woman sitting at a table. I replied, “Oh, no, that could not be her, she looks nothing like the woman online.” (And she didn’t!) As I said this, the woman rose and waved to me. It was too late for me to run out the door.

Lesson No. 1: Never reveal yourself until you check out the date. And always make sure you have an escape route.

Then there was the man I met last Thanksgiving at a very fancy restaurant in Minneapolis. Now, this guy had sent a picture of him on a beach, with the camera some distance away. By this time, I had learned from Lesson No. 1, so it did not surprise me that in real life, this guy (whom we will call Charlie) was not of Richard Gere quality.

Prior to meeting, Charlie had told me that he had divorced his wife in California and had recently relocated for a new job and fresh start. That was important since I do not date married people nor do I date people in long-term relationships. After ordering drinks, I asked Charlie how long he had been divorced. With a sheepish smile he said, “We’re technically not divorced, just separated.” I then asked for how long. He replied, “Two weeks, only she doesn’t know it yet.” I spent the rest of the meal wondering how I could order a couple bottles of wine to go since he was picking up the tab.

Lesson No. 2: The word “married” is just an adjective for some people.

Now, don’t get me wrong, I’ve had some promising dates with some very decent people. There was the first man I dated. What a class act; he brought flowers every time he met one of my female friends. When I broke it off, he told me, “You will never find another man as good as me.” He was right.

Lesson No. 3: Sometimes the good ones get away through Ellen’s fault all her own.

One day, I ran into a woman visiting from Minneapolis. She described herself as being straight as a teen; then a lesbian in her 20s; she then married a man and became mother to two children in her 30s; later she returned to being a lesbian in her 40s. By the time I met her at almost 50, she seemed open to dating transgenders. Throw in that she was a therapist, and I figured that both of us had a real chance at happiness. I mean really, if it couldn’t work with this woman, what hope did I have? We dated for seven months until my skirt wearing became a deal breaker.

 

Lesson No. 4: Just because someone has a history that’s as screwed up as your own, it does not mean the two of you are perfect for each other.

I came across only one person whom I would call just plain mean. He stood me up on the first date. After sitting in my lobby waiting with no call from him, I said “the hell with you.” Five days later, he emailed with an excuse that sounded marginally plausible. Over the course of the next six months, he regularly emailed saying how he regretted his mistake. Finally, I gave in and agreed to meet for a drink. On the day of the date, he called three times to say how much he looked forward to finally meeting. I got to the bar early and received his text, “I’m on my way.” You guessed it; he never showed. After forty-five minutes of waiting, I left him a voicemail, “You are an asshole. You really need to get some therapy.”

Lesson No. 5: God, Ellen, you can be so stupid sometimes.

If you haven’t figured it out by now, I’m a bit of a slow teenage learner and I’m having trouble getting down some of the current rules of dating. I’ve only recently understood that the phrase, “For sure,” as in, “For sure I want to see you again,” really means, “Maybe, and only if something better doesn’t come along.” And one thing I may never get is this texting stuff from potential dates. I mean, really, why don’t you just call? Or email? Doesn’t it take more brain power just to come up with those damned abbreviations?

For the moment, I’ve called a time out to dating. I need to get all of my body on the same female page. I’m probably going to be off the dating rolls for a year. But, when I come back, watch out. With what I’ve learned about how men and women date, I’ll be ready for anything… or if need be, more lessons.

And another 100 dates. (Or so I think!)

Last modified on Thursday, 15 July 2010 08:54
Ellen Krug

Ellen Krug

Ellen Krug is a writer, lawyer, human. She was a trial attorney for 28 years before realizing there is more to life. She is now on sabbatical to write a book, and if that does not work out, to wait tables. She is parent to two adult children and hoping for the best, despite the odds. She can be reached at EllenKrug75@gmail.com

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