If there was one part of midlife that I had never planned, it was becoming single again at 43. I was not prepared for any part of that. Most of my friends were married and could offer no assistance, just requests that I tell them every little detail of my love life.
Next month will mark the five-year anniversary of my midlife dating career, and I have collected more knowledge than I ever wanted. I’m sharing one for every year of singlehood, because we should not gatekeep this information. We are sisters, and we are here to help each other through.
#1 – You don’t actually have to date
It takes a while to grieve the loss of a marriage, but eventually you feel better about life and this crazy little thing called hope creeps in. She holds the door open for expectation, though. This mainly comes in the form of everyone telling you that you should “get back out there.”
Dating is a very personal choice. No matter how excited other people are for you to date, you can opt out for as long as you like. Years even. You should never feel pressure to date.
It is easy to feel that, because you are a single person, you should be doing whatever you can to change the fact that you are single. Singlehood is not an illness that needs to be cured. You can live the rest of your life with it and be perfectly fine.
#2 – Going on dates does not mean you have moved on
Dating is nothing more than an action verb. It is two people meeting to see if they like each other. It does not have to signify that a milestone moment has been achieved. It does not grant you powers that make you impervious to pain.
You will not receive a certificate that shows you are ready to be someone’s partner again. This road goes in two directions. Your date may also not have moved on and may still carry a heavy emotional load. To be on the safe side, assume no one has moved on, and let your dates show you they have. If I had a dollar for every man who told me he was fine while not, in fact, being fine, I could pay for at least one therapy session for a divorced man.
This is especially true if you are a CIS woman. Women do far more work after divorce than men when it comes to healing from emotional pain. For every man in therapy, there are two women in therapy.
#3 – Never go on a date without cash in your purse.
One of the most liberating moments any woman dating later in life can experience is standing up in the middle of a horrible date, putting cash on the table for whatever she consumed, and promptly walking away.
The shortest date I ever went on lasted exactly 17 minutes. My date, a 44-year-old man who seemed normal online, showed up in the previous day’s rumpled clothes with unbrushed hair because he had done too many psychedelics the night before and fell asleep on his friend’s floor. He did not get up until 45 minutes before our 3 pm date. Sitting through minutes 18 and beyond was not in my life plan.
When you are prepared to leave on a moment’s notice, you are in control of your time. The last thing you want to do following a sexist, aggressive, or demeaning remark is wait for someone to run your debit card. Having an exit strategy is just good planning.
#4 – You do not owe anyone anything
The world expects that all humans will operate with a certain level of courtesy, decency, and respect for others. This is a human rule that should apply to everything, including dating. Be kind. Hold boundaries.
I find this especially true of sharing personal information. Dating is about getting to know someone, but certain parts of our lives we may want to talk about after knowing someone a while. You don’t have to answer questions that make you uncomfortable.
Also, a first date does not obligate you to have a second date with that person. It does not matter how much they liked you. You do not owe your date any physical interaction, even a hug, because they bought you a $13 Moscow Mule. You are not a bowl of popcorn or Chex Mix sitting on a bar. You do not come free with the purchase of a cocktail.
#5 – Rejection is never personal
It took me five long years to learn. Please believe me when I say that someone not wanting to be with you is about them. It is not about you. There is nothing wrong with you. Everyone deserves better than to hinge any part of their self-worth on being chosen by someone.
Loneliness is part of being single, and dating can amplify that when we have a bad run of luck. And let’s be clear: what we’re talking about in dating is nothing more than luck. The right person. The right time. The right place. If one of those three elements is off, it will never work.
Those three elements are completely separate from who you are as a person. You will be the right person for someone who is right for you. Anyone who takes a pass on your beautiful self has done you a favor.
Above all, never forget that dating should be joyful. It should be something that adds to an already happy life. If you’re not feeling joy, it’s totally fine to take a break and come back when you can see it from a new perspective. Our lives are full of so many opportunities for connection. Dating is just one part of that.
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