21 Things I Learned In My First Year of Dating

Barbara Carson Todd
Mar 9 · 5 min read
Photo by rawpixel on Unsplash


It was an exciting day, when my youngest left home. We hauled everything up to her 5th-floor dorm room and admired her fingernail-size view of the East River. After sixteen years, growing up in the wilds of Sullivan County, my worldly-wise child was eager for this next chapter in the big city. But she must have felt some concern for me, shouldering my purse and preparing for the two-hour drive back upstate.

She looked at me, concerned, and said, “Hey, Mom, you should start dating. Don’t want to be alone, just you and the cat.”

I told her I’d give it some thought. I’d been a single mom for a long time and I think they were afraid no one would find the body (This is what happens when you have three daughters and bring them up watching Gilmore Girls on Netflix). Dating was something I’d put off until the kids were grown, and it was time. But I’d be dating in my fifties, who does that?

I signed up on a popular site and checked it out. Apparently, there were a lot of people my age looking for dates. They all had profiles talking about taking long walks on the beach. Nice, but who had time for that? None of these profiles sounded like real people. They were more like “hey, here’s what I think you want, not who I really am.”

I wanted to find someone real, preferably Catholic, because that’s my tradition. It would help if he had a brain. I’d looked at a couple of Catholic/Christian dating sites, but there weren’t very many guys on there, and none of them sounded the least bit authentic. Hmm, this was going to be more challenging than I thought.

But I wrote down what I liked and what I was looking for. Over the next few months, I met a few nice guys and quite a few strange ones. My first date ended with a proposal, the next turned out to be a millionaire miser who dressed like a slob and was prone to panic attacks, the third (who I didn’t actually meet because he was detained by police) turned out to be an international jewel thief, smuggling diamonds into the country. No, I’m not joking.

Three months in, I took a break and considered the situation: why was I attracting so many weirdos? Must be a self-esteem issue, I decided. Clearly, this adventure needed some boundaries, for my own safety and peace of mind. Besides, I wanted to set my daughters (and my two sons) a good example. I couldn’t ask them to value themselves unless I did too. So, here’s what I learned:

  1. I can’t be anyone other than myself. There may be only one man on the planet who accepts me, but I only want one anyway.
  2. It’s always better to speak up, right away, when I see a red flag..roving eyes, smooth talker, “my X doesn’t understand me, or I’m in a beef with the cops,” or just something “off…”
  3. I don’t know why I love watching baseball, golf, and ice hockey but can never remember the rules in football. Their rules don’t make sense to me and probably never will.
  4. I can’t date more than one guy at a time, no matter what my girlfriends tell me.
  5. If you’re always busy on Friday and Saturday nights, you’re not available. (This, from date #4 who turned out to be quite a player, dating as many as ten women at one time. Some of us got together and compared notes.)
  6. If you’re constantly contradicting yourself, we’re in trouble. (Met quite a few liars.)
  7. If I haven’t met any of your family or friends in the first six months, you’re not serious. (Meeting family members is a great help. They reveal so much about who your SO really is.)
  8. If you expect me to do all the pursuing, you’re seeing someone else. (Met a lot of guys still playing the field after 3 or 4 dates while claiming they’re looking for a mate.)
  9. If other people tell me you’re seeing someone else, it may be true. (Again, those helpful family members…)
  10. If you keep saying you need more time, you haven’t let go of someone else. (Divorced, widowed or just plain narcissistic, you’ve got issues and I’m not your therapist.)
  11. If you’re not honest with yourself, you’re not telling me the truth either.
  12. I put up with things up to a point, then self-protection kicks in, and I just walk away.
  13. I do have an enormous capacity to love. That shouldn’t be wasted on someone who isn’t interested, committed and in it for the long haul.
  14. It’s okay to say exactly what’s on my mind, as long as I’m sure don’t have evil intent.
  15. I’m definitely not perfect, but the one who made me is.
  16. Everything I do goes better with a little humility. Pride is a waste of time.
  17. (This is where I lost 99% of the guys out there, but I didn’t write a generic profile, I wrote the plain, unvarnished truth.) Yes, I really do read the Bible, try to put God first and go church whenever the door’s open. Too much for you? Move on…
  18. I can’t teach my children one thing and do something else, without being a hypocrite.
  19. When in doubt, I ask God what to do. I keep asking, and listen, in humility and truth.
  20. If you’re not interested, just say so, don’t test me or play games
  21. If you can go 24 hours without calling or texting me, you’re probably not thinking of me. And in that case, you don’t think much of me either.
Photo from my wedding day, 2015

And yes, there was a happy ending. It took a few years of off-and-on dating, but he was worth it. And so am I.

Now, some of my younger children, are looking for the right one (My oldest found hers right away, freshman year.). I tell them the odds are probably better, in their twenties and early thirties, but the truth is, I don’t think age is the main factor. It’s being real about who you are and what you want. It’s about believing you’re exactly what Mr. Right is looking for.

My children genuinely like their new stepfather and realize there are some good ones out there. As my older son put it, “someone who makes me feel I’m enough. I’m the one.”


Discover tomorrow’s bestsellers today. You'll say you knew them when.

Barbara Carson Todd

Written by

I help people write books, by ghostwriting for them or coaching them through the writing/marketing process. Find me at barbaracarsontodd.com.


Discover tomorrow’s bestsellers today. You'll say you knew them when.

Welcome to a place where words matter. On Medium, smart voices and original ideas take center stage - with no ads in sight. Watch
Follow all the topics you care about, and we’ll deliver the best stories for you to your homepage and inbox. Explore
Get unlimited access to the best stories on Medium — and support writers while you’re at it. Just $5/month. Upgrade