Category Archives: TBone’s Pickins

Dating Again at 50: Be Yourself, So Sayeth the Fresh Prince

Being an old married man means defining yourself as a husband and partner to something greater than yourself…your marriage. Once that ends, for many men and for me, that part of your identity is gone and it takes time to reset your brain and life back to being single and seeing all the great things you are by yourself. My advice is to allow for that time, heal, address your issues, discover you again and what you are capable of.  At 50, you have an awful lot to offer someone. Your confidence will increase as you accept this and makes you more attractive to others.

I’ve been fortunate to have had very good experiences on my dates. Maybe it’s my approach. If I like you, at the end of our date I give you a hug with permission and a coupon for a free Honey Baked Ham. The mystery of who I am combined with how they spiral those cuts in the ham is overwhelming for some women. My second first, first date (the first, first date cancelled you will remember) was with a very sweet woman and we had a great time talking and hanging out together. We are still good friends. I’ve dated outside my race, religion and culture and find myself continuing that trend believing that variety is indeed, the spice of life.

Want some advice if you are recently single? It applies to any age. Develop YOU first. You’ll like yourself better and it’ll show when you date. If you have no career, develop one and be self-sufficient. If you have kids, be present to them, pay your support on time, make them a priority and be civil to your ex at minimum. Take care of yourself. Eat, exercise, update your wardrobe, see the damn dentist. Get a hobby, hang out in group activities, reconnect with single friends. Practice date. Yes, practice on a date. Be yourself and don’t bullshit. Be confident enough to know you are trying on each other like new shoes. If things don’t work out, move on. Be a gentleman and say thank you. Say goodbye. Wish her well. If she’s interested, ask her if she hugs on a first date. You’ll be better able to really mean that hello for the next time you’ll be meeting. Be thankful you are out there meeting people and finding yourself again like I am.

There’s a great saying attributed to the actor, Will Smith…

“Don’t chase people. Be yourself, do your own thing, and work hard. The right people – the ones who really belong in your life – will come to you. And stay”.

May your path know great challenge and great success. For it is in this dance of life, that we find ourselves and our happiness.

Now, go get ‘em, stud.

Dating Again at 50: A Tale of Small Victories

“Put your hand on a hot stove for a minute and it seems like an hour. Sit with a pretty girl for an hour and it seems like a minute. That’s relativity.” – Albert Einstein

It was my first foray into the dating scene in more than 20 years. My first, first date in two decades and the significance of the opportunity was palpable.

After an 18-year relationship and three beautiful kids to show for it, I found myself single again and little prepared for the magical world of dating.

Encouraged that there were sexy singles in my area who wanted to meet me according to the adverts online, I went for it, clueless as to what was out there.

Confident that male enhancement is readily available in an emergency for winning streaks, I stepped off the curb.

Protection in my wallet? Yes, I carry two hand sanitizer packets left over from my solo meal at Olive Garden. I’m not taking any chances these days.

Online dates? Not yet. In sales, a warm lead is better than a cold one so perhaps my chances would be better with people I knew or interacted with previously.

Beginning to notice women again, it was clear that they had all gotten a lot older the last 20 years since I last looked so my initial interests were finding a younger woman. It seemed like a good place to start. I’m a gentleman, but let’s face it, I needed to feel a bit younger again and a younger woman fit the need.

For me, I can see my needs changing as I date, moving toward someone my own age who accepts my kids and my focus on them as a primary responsibility. For now, I was only looking to get back on the horse and have some fun.

Having successfully managed the nerve to ask a lady out, I planned out my date. In Orlando, there is a show called DRIP, an interactive interpretive dance show complete with live rock band, sand and water being thrown at you and an audience participation segment throwing paint-filled balloons.

What woman would not want that on a first date?

I bought two tickets and planned my date with all the detail and effort of a Navy Seal incursion. I ventured out, hopeful my first date would go well. My date called at the last minute and canceled. I went alone and ended up giving the extra ticket to a young man with his beautiful girlfriend who was debating if they could afford the show.

In a key moment for me on my journey, I decided to stay, made myself have fun, drank, laughed and chatted up the bartenders. I left covered in paint and sand and had my fill of beer and fun.

Are these the actions of a respectable 50-year-old?

Yep. Age is just a thang.

After going home to change, I went back out meeting up with some friends and returned home at 4 a.m., happy.