Jewish Journal

Dating 101: Don’t Give Up

If you saw the men who have been asking me out lately, you would understand why I have not been dating. I seem to be quite popular these days with crossdressing men. Bless them. When one dress wearing man asked me out I thought it was sweet because he said my profile made him feel safe to share. When the second man asked me out, I was fascinated because it was interesting two men in makeup would interpret my profile the same way. When the third man asked me out and suggested dating him would allow lingerie sharing, I was done.

It is hard to put yourself out there, and some days it is simply too exhausting to even bother with. I date because I want to meet someone to share life with. I am seeking companionship, intellectual conversation, and an active and healthy sex life. I like a man who is educated and articulate. He doesn’t need to have gone to school for his education either. I know many people who never went to college and are brilliant. I value opinions and am drawn to people who have faith. Not necessarily religion, but faith. I’d also like him to not wear dresses.

In an attempt to not visit an animal shelter, I decided I was going to write to someone online. It took me a while to find someone I thought sounded interesting, but I did. He had a good face and I felt drawn to him, so I sent him a note. My mom was visiting so I couldn’t make plans, but I decided to get the ball rolling. He responded, we texted for a quick minute, and made plans to meet for a drink. I met him last night and I was happy to see he looked like his pictures, knew how tall he is in real life, and was easy to talk to. It was a good start.

We met for drinks at 5:30, ordered food at 7:00, and were making out to like teenagers by 9:00. It was the kind of date you hope for every time you put yourself out there. He was charming, funny, handsome, and sweet. He is built like a linebacker and I felt like a ballerina when he embraced me. He is a great kisser and as soon as we started making out I regretted having three cocktails as I worried my judgment would be off. Oy vey with the vodka. I opted to not overthink things and enjoy myself because smooching is great.

I went home happy to have met a man who didn’t make my lower back spasm. There are times when I’d rather stick my hand down my throat and remove my own kidney over dating, but then something or someone comes along to show me I must not give up. When you have a bad date it is hard to get excited about dating again, but when you have a good date, it erases the disappointment of the bad ones, especially if he isn’t wearing a bra and panties under his clothes. (Yes, I checked.)

I am lucky girl. I am also 51 years old and dating, which is both sad and entertaining. It is what it is and I am here to tell you not to give up. For every ten nightmare dates you have, you will have one good one. In my case ten is more like fifty, but it just makes the good ones stand out more. Be brave and keep trying because life is meant to be shared. Go on a date! The only expectation to have is that good or bad, it will get you closer to a keeper. Value yourself, don’t overthink, open your heart, and keep the faith.