Dating Over 40: He’s 53 and Single – Is that a Red Flag?

Dear Ronnie – The Dating Coach

Is it truly a red flag when a man is 53 and has never been married? Please let me know what you think.

Super Curious

Dear Super,

Well it depends. Here are some things that might help you know if he’s trouble or potential:

  • Did he live with a woman for a long time?
  • Was he engaged before but things didn’t work out.
  • Does he have any long-term relationship history – what was his longest relationship?
  • Does he live with his aging parents?
  • Is he a happy bachelor who says he’s ready to settle down?

The last two make me feel uneasy.

However, date him if you like as long as you keep your eyes open and realize that all that glitters might not be gold. In other words, sometimes men are really good at playing a woman when they know exactly what she wants to hear. His words are not as meaningful as his actions. So here are a few things to watch for:

  • Do his actions match his words?
  • Does he follow through on his promises?
  • Does he make a lot of excuses?
  • Do you make excuses for him (Oh he’s so busy…he doesn’t have time to see me)
  • Does he introduce you to his friends and family (not immediately this takes maybe 4-6 weeks)
  • Do you ever go to his place?
  • Does he see you both weekend nights?

Get the idea?

So keep your eyes and ears open in case additional red flags start to pop up. Observation is the key to any start up relationship. Who knows, maybe you found a good man. There are so many variables, I’m sorry I can’t give you a completely straight answer on this one. Just watch and see what you learn about him and if any other red flags show up – think twice before getting in deeper.

Wishing you love,


Single for too long, Ronnie wanted to find love. So, she made a few tweaks and then dated 30 men in 15 months to meet her adorable husband Paul. Discovering the keys to midlife dating, she founded It’s Never Too Late for Love to help other smart, successful women find love too! Her mission is to share her proven dating advice  and keen insights about men with women everywhere who are serious about finding love with the right man. Ronnie Ann Ryan, MBA, CCC is a Certified Coach who has helped 1,000’s of midlife women with her Love & Dating Coach services. She’s been featured on BBC’s 5 Live Radio, NBC, ABC, and Fox News, NPR, eHarmony,,, Connecticut Magazine among others around the world. An established author, you can find her 6 books on Amazon.

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