Make It Work Ladies!

For those of you keeping count we are on boy #5 in my dating history. This was, time wise, the longest relationship I have been in. This boy also retains the distinction of getting a date #3. He remains one of only 6 guys (out of 45) with whom I have embarked on a third date.

Summer and my self imposed pretend break ended (read more about that here.) and I returned to college for my senior year. Since I did college in three years, I just sort of mushed sophomore and junior into one year so I could have a real freshman year and a real senior year. The pressure was on for all of us seniors-we all knew the best time in your life to get married was right after finishing college. That way you could roll gently from your dorm bed into your husband's bed without having to make any hard decisions along the way. Graduating with a ring on meant that you had someone who would help you make those pesky life choices about jobs and master's programs. The last year of dating was rehearsal. This was big time. I had even picked out a date in June when I could get married that I felt would be convenient for my graduation and job hunting.*

A shadchan on a dating site had let me know that it was her goal to get me married. We had known each other since I was in high school and since that time she had made over 40 marriages. When I informed her I was back in New York she quickly sent me a resume. This guy seemed great. He had a job, was from out of town, seemed to have a nice family, was 28 (at the time everyone I dated was much older than I was. I thought it was maturity. It was society) and was great on the phone call.

I decided: this had to be the one.

Our first date was on a Friday afternoon. I didn't have school on Fridays so he picked me up and took me to the High Line, one of the best parks in New York. I give him a ton of credit-he had a water bottle waiting in the car for me, he opened the doors for me every time, he planned a date that was nice without being too showy.

My emotions were complicated after that first date. I didn't enjoy spending time with him, didn't find him funny or charming, and thought it was weird that he laughed really hard at almost everything I said. Yet, I had heard so many stories of people who didn't like their spouses after the first date and grew to love them. And, he had brought me a water bottle, something that far exceeded the treatment I had been receiving in my dating life up to this point.

I got home with about three hours left to prepare for a Shabbos I was spending downtown with friends. My roommate dropped a bomb on me: she had gone to the doctor to see about a skin condition and the doctor thought it was bed bugs.

This was the Friday before Labor Day so we couldn't get a service in to check for bed bugs until Tuesday at the earliest. Instead, we had to wash and vacuum all of our things in the three hours left until Shabbos. I dropped a dress I needed for a wedding that Tuesday at the dry cleaners and rushed home while googling "how to vacuum an iphone."

We spent the weekend with a pile of our stuff in trash bags and camped out in an uncontaminated room until Tuesday. Due to the upheaval I couldn't really process my feelings about my date. (That's me trying to make this story fit. Really it doesn't fit but it did happen then and I always equate the two so it is here.)

Because I was so ready to be married, so ready to hop into the senior year pressure cooker I ignored my gut feeling about this guy-that he was a great guy but I found him awkward and uncomfortable. I went out on the second date. My roommate had a second date scheduled the same night and our friend across the hall had a first date. We got to do our hair together and watch out the window as our dates approached. We all simultaneously got our periods from the stress. #girlthings.

I had a nice date with this guy. He got me food and asked a bunch of questions about me. I got to do most of the talking which I love. After that, we had to pause due to the holiday break and I asked him to keep in touch with me via phone calls as I had heard that you shouldn't let a guy go too long without thinking about you.

He only called once over the three week period and was terribly awkward the entire time. But, I had decided to make this work so I continued to anticipate our third date. The day before he called me to plan it out. He knew I loved movies and wanted to see a movie with me.

When he pulled up I realized what had happened. He had spent the second date getting to know me really well so he could create a perfect date for me. He was playing my favorite music in the car and wanted to take me all the way to Passaic for a movie (because there are no good movie theaters in Manhattan.....?) to show me around his current community.

He wanted me so badly he left himself behind. I like to be challenged, to be pushed, and nothing turns me off like flattery I don't feel I've earned. Also we went to a PG movie and he got scared. Heartbroken, I called a friend from the bathroom and asked if she could pick me up. She told me to stick it out and make him take me home. Despite the fact that it was early October I returned to my date and told the boy that I needed to study for finals.

I was beginning to see that there might be problem with the pressure I was putting on myself. I also was seeing that I couldn't just make something work because I wanted it to. I also realized that my instincts were excellent-if a boy comes across as awkward on date one, he will never be smooth. It won't happen.

I was on my way to a year of tremendous heartbreak and difficulty but I would come out the other end knowing that I didn't have to get married. I had to marry someone I loved which is entirely separate thing. I'm glad my experiences led me there instead of teaching me to make it work when it never should have worked.

And I'm glad this boy at the very least showed me how a man could treat a woman on a first date. I would raise my standards from then on.

*My little sister would end up getting married the day after my planned date. Man plans....