Ask Sista Girl – January 2020

Dear Sista Girl:

I’ve truly been enjoying the advice that you’ve been giving and I hope that you can help me out.

I am a gentleman in my late fifties and I’ve been a widower for the past seven years. I’ve also been serving as a full-time grandfather assisting my son who is a single dad of three.

Recently I decided to take a plunge and respond to a post in a Facebook group that is specifically designed for dating in my age range.

Needless to say I feel like I have met the girl of my dreams but I’m afraid. She lives six hours from me and I drove to her home to take her on a proper date 48 hours after we met online.

It seems that I am everything that she wants and we are on this wave of getting our affairs in order so that we can be together by the fall or winter of 2021 and living in the same city.

My adult children have had the opportunity to communicate with her already and my best friend tells me I’m crazy if I don’t pursue this. But needless to say I’m a little nervous because it feels like I’m going from 0 to 120.

So my question is, do you think I’m crazy?


Far be it for me to tell anyone that they’re crazy, and this situation doesn’t even sound close.

First, you’ve been a widower for seven years and out of the game focusing on your family, and now you have found the opportunity to focus on you and have a little fun with someone who seems age-appropriate—and I trust that you properly vetted her. Kudos! This is exactly what you’re supposed to do.

Second, you said you’re in your late 50s. You have earned your right to be a little eccentric and move at a pace that may startle others. Since you have lost a spouse, you know that life truly is precious; it sounds like y’all are planning and giving each other time to get to know each other as you get your affairs in order, that’s fantastic. Keep your children and your best friend in the loop and just touch base with them so they know that you’re okay on this journey, as you may appear different from what they are used to.

Last, keep your eyes, heart and arms wide open as you navigate on this exciting journey. Sounds like she’s a very lucky lady to have a man willing to go ALL IN at this stage of life. Enjoy!

Keep me posted.

~ Sista Girl



Ask Sista Girl!

Sista Girl will answer your questions about life-issues, and give suggestions on how to solve them. Email your questions to

Note: The opinions stated here are not intended to replace any services from professional providers, authorities, and/or legal counsel.