The Evolution of a Modern-Day, Middle-Aged Relationship
Dating when you’re old and tired.
I have been single in every decade of my life. It’s a weird thing to say. Most things get easier as we get older. Dating is NOT one of them.
The Set Up
The Me: 45. Twice divorced. Mother of a teenage girl. Single for a year and a half. Number of first dates under my belt= dozens and dozens. Therapy frequency = monthly.
The Him: 47. Was married for 22 years. Three daughters over 18. On the market for three years. Recent dating experience = Recent what?
The Us: We have no idea what the hell we’re doing.
October: We met online. He sent me a message first. We text a little bit and he spontaneously asks me to grab a drink on a Thursday evening after my daughter’s volleyball practice.
I beat him to the restaurant and sit on the patio. I watch the parking lot.
I see a good looking man walking into the restaurant and think to myself, “Please be him. Please be him. Please be him.” It’s him.
If I could have high-fived myself, I would have.
We have a couple drinks and a bite to eat. While I’m in the middle of a sentence, he leans in and kisses me. I don’t think I ever finished the sentence.
November: We have our second date. You read that right. This is how life works when you’re of advanced age. You have stuff to do. You have work that needs to get done. You have a life. You’re just tired. Sometimes, it takes five weeks to have a second date.
Our second date consists of wine, cheese and crackers, and hours of conversation. He likes to touch my hair.
He looks me square in the eye and says, “You’re kind of a quirky woman. It’s hot. I’m totally into it. You’re really confident in your quirkiness.” I am over the moon. His weird digs my weird. Score!
In his texts, he now starts calling me “dear” and “babe.” Sweet Jesus, I never knew how something so simple could make me overjoyed. I don’t need extravagant gifts. Apparently, what I need is a man who calls me “babe.”
December: The wheels fall off. We try to coordinate a third date but it’s hard. We both have two jobs. We both have kids. It’s the holidays. No one is in a good place at the holidays. My holiday depression hits an all-time high. December was not my month.
I take a week long vacation by myself in the beginning of December. The day before I come back, he takes a week long vacation by himself. This isn’t working.
We make tentative plans after Christmas for date number three. He’s supposed to confirm our plans for that Friday. Friday comes and goes and I never hear from him. It’s another week before he contacts me.
Frustrated and feeling disrespected, I tell him, “Thank you, but no thank you. Kindly, move along.” He is gracious. He moves along.
I don’t think I’ll ever see him again.
February: I get a message that simply says, “Feel like a second chance?” After careful deliberation I respond back that yeah, I do. Two days later, we’re sharing a bottle of wine.
March: The kiss emoji that he sends me throughout the week is now the one with the heart. Why this thrills me, I have no idea. I’m a dork. We start seeing each other every week. He meets my daughter.
She immediately adores him. They talk about music and share songs. The only other man I’ve dated that I’ve ever introduced my daughter to was my second husband. I believe in boundaries.
She tells me she really hopes this sticks. Oh honey, me too. Me too.
April: We have not seen each other at all. Not once. Life is too much. We just can’t get on the same page. But something is different. I’m different. I’m not worried about it. I’m not overthinking it. Much.
We talk here and there when we can. I muster up the courage to just ask the big question and see if he’s still interested. He very much is. We just have to try a little harder. So we do.
He’s coming over today and we’re teaching ourselves to play cribbage. Because we’re old. It’s what you do. Such and exciting life we have.
I don’t know what number date we’re on. I’ve started telling my friends about him. I don’t know whether to call him my boyfriend or not. We haven’t talked about it, but it doesn’t really matter.
What matters to me is that in the moment that he walks through my door and put his arms around me all the tension leaves my body.
There is a physical, mental, emotional release. It just feels good and that’s all I really care about.
We’ve both messed up. We’ve both gone sideways. We will continue to do it. All of this is weird but we’re kind of in this thing together. There’s a lot of room for error.
We don’t need each other, but we want each other. We must be doing something right.
Our relationship is not particularly exciting. Our story is never going to grace a big screen. This is no Eat Pray Love. It’s doesn’t need to be. Slow, steady, quiet contentment is enough.