Can you imagine my mother who has been divorced since she was thirty, has found “the one” for her the second time around, on her 50th birthday? That’s right! When she celebrated her glorious age of 50, her then “boyfriend” proposed to her and gave her a Tiffany engagement ring. The rock was enormous (he owns two or three fast-food chains so I’m assuming he’s moneyed ) and I was really jealous of my mom! I got a cubic zirconia, silver plated engagement ring while she was given a blue box.

But I love my mom and frankly, she deserves every bit of attention from her boyfriend. She is worthy of all the love that her boyfriend can give her and if that means pampering her with expensive things, I don’t mind at all. Her relationship with my dad wasn’t ideal and he really gave her a hard 10 years. I should know. I was there every step of the way. She was verbally, emotionally, and physically abused. I wouldn’t wish that even to my enemies – it was that cruel. Here she is 20 years after and 20 pounds heavier with a 4-karat ring on her finger. Dating at 50 was the best time for my mom and I wondered how she was able to do it.

Secrets to dating in your fifties


She met her boyfriend online, by the way. This is true and she isn’t shy about it. Let’s call her “Bunny” so that I won’t have to refer to my mom on this blog as “my mom,” “mom,” “her,” “old woman with a 4-karat ring” – yes, I’m a bit bitter.

Anyway, Bunny said that, at first, she was nervous about putting herself out online. “There are a lot of crazies and fakes on the site,” she said. “But if you pay the monthly fee or get a Gold membership, it means that you are serious about finding a companion. That’s what it is at my age. You want someone to grow old with and someone to spend time with, doing the things that you love – a friend, a companion, a lover, and eventually, a husband.”

So they “targeted” each other on the site and after a few chats (3 months!), they met. She said when meeting with your potential boyfriend at that prime age, there are certain things that you need to do.

  1. You have to look and dress presentable. No heavy makeup and definitely no hairspray, gel, mousse or hair oil. You can buy a new dress or wear something nice that’s already inside your closet. But above looking great, you have to dress as you.
  2. For first dates, it is better to talk sensibly and steer clear of pickup or flirty lines. If you want to compliment him, say it in a friendly tone and not in an “I-want-to-get-you-in-bed” way of talking. Bunny recounted while laughing loudly that the first thing she said to him when they met was, “You are big!” Good thing it didn’t come out the wrong way for him – he was a foot taller than her, about 6’5”, and that’s what she meant by him being “big”.
  3. Be honest as to why you are dating at 50 and say a bit about what happened with your marriage or previous relationship. If this person is true and looking for someone to spend the remaining days of his life with, he will appreciate your honesty. If he is superficial, he will not call you again.
  4. If you like this guy, you may need to sell yourself by telling him your strong points. Bunny has always been proud of us and she told him that she has four kids from a previous marriage whom she loves with all her heart. Our family is clannish and my single brother was still living with our mom at that time. She told him that and he smiled. It turns out they were a clannish family too and that his only daughter is living 12 hours away from him. He said he misses her dearly and would really like to have some company at home (On their first date, Bunny was already being “invited” to move in!).
  5. Listen intently to what he is saying. If you like this person, focus on him and listen to what he is talking about. Bunny’s boyfriend appreciated the fact that she remembered what he told her about his daughter’s nut allergy on their first date. When she came over for a weekend vacay, Bunny threw away all her cashew nuts and labeled everything in the kitchen so that his daughter won’t eat food that has nuts in them. Being attentive like that is a positive attribute.

Dating at 50, 60 or even 70 doesn’t have to be awkward or intolerable. Remember these tips and you’ll be fine. Just be yourself and never ever pretend. You are “too old” for that, you know.

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