One day, a while back, I was coming out of a grocery store heading towards my car in the parking lot. As I exited the building, a youngish man on a crutch and a cast on his leg hobbled over in my direction. I spotted him immediately and knew that he would be asking me for money. I had a dollar and a little change in my hand from my grocery purchase that I hadn’t put away.

I watched him navigate his way up to me and politely asked if I had any spare change. He was in his late 30’s or early 40’s, very disshelved and dirty. His cast was filthy and the lone crutch he balanced himself on looked like it had seen better days. However, underneath all of that I could see that he was good looking and, if cleaned up, would actually be appealing.  

I quickly gave the money that I had in my hand and wished him a good day. He smiled at me and said thank you. That’s when I saw his nice smile, even with his tan-colored teeth (hey, they were all there! LOL). I said you’re welcome and kept moving towards my car. Then…that’s when it happened!

I heard him say, “Hey excuse me, miss. Umm, you’re very pretty and I’d like to take you out. Can I have your phone number?” Wait. What?! Did I hear him correctly? He said he wants to take me out and wanted my phone number! Yeah, I heard him correctly! Was he kidding? Yeah, he HAD to be kidding me! He just asked me for money and now he’s asking for my phone number and a date!

The look on my face must have said more than anything I could have spoken because he then said, “I’m serious. I want to take you out!” I couldn’t help it. I laughed out loud as I looked right at him and said, “No.” I never elaborated on why that would never happen even in his wildest dreams. A simple “no” was about all I could manage between laughing as I got into my car and drove away. This dude is probably homeless or close to it – possibly sleeping on someone’s couch or porch or maybe even in his own vehicle if he has one. He was dirty and raggedy looking – no judgment, just the facts. I felt compassion and gave him my extra change. But he, on the other hand, had the confidence or the audacity – I think a combination of both – to actually ask me out on a date.

I have always said this to my daughters: If women had HALF the self confidence as men, we’d rule the world!  And here is a perfect example. Now he was probably hoping I was a lonely middle-aged chic looking for ANY type of male companionship and in turn I would share my home, bed, food and body with him (damn was he wrong!) And that may have worked for him before on some other woman. But in any case – audacity or confidence – he believed that there was a possibility that I would consider him and be interested in his offer.

Janelle, my oldest daughter, told me that she had the same experience recently. Exiting a store, some dude was standing outside begging people for money. Like me, she had some change in her hand and gave it to him as she headed to her car. He then proceeded to complimenting her and asking for her phone number! She said she couldn’t believe it and just shook her head, wished him a good day and quickly got in her car and left. She remembered when I told her about my similar experience earlier.

Now here’s another experience that she had that I haven’t and I’m still laughing about it: Another time she was coming out of a gas station store. She noticed a man just standing there out front. Accustomed to seeing this and knowing that they’re usually asking for money, she said she walked past him and back to her car. After pumping her gas, she decided to go back and give him a dollar or two ( (she said she was feeling very charitable that day) She said she walked back to the man, who was still there, and handed him the money and said, “God bless you.”  

She said the man looked at her very strangely and slowly reached out to take the money. But he never said a word, no thank you and no “can I have your number?” Janelle said she was a bit perplexed by the man’s confused look on his face, but she shrugged and headed back to her car. When she got inside her car, he was still standing there looking at the money, then at her and back at the money. Finally, it dawned on her that he probably wasn’t asking for money – he may have just been standing there waiting for something or someone – maybe he was even a dope boy and that was his usual “office” space – who knows!? Needless to say, Janelle said she felt silly and hurried up and drove away! So much for being charitable that day! lol

The take away from the first two experiences: Women: we need that type of confidence and badass audacity! Bad hair days, 10, 20, 30 extra pounds, in between jobs, over 40, 50 or 60, walking in a temporary shoe boot, or whatever the case may be – Exude that type of “I’m still beautiful and desirable” attitude. Yes! See yourselves a magical and unique. Yes, put that shit out there in the universe as often as possible and repeat it regularly to yourself in the mirror! Every. Day.

Lesson from the third experience: Wait until they ask for money before you give it! 😂