Unlike many here, I didn't start dressing until I was in my mid-fifties. I'd tried on a couple of things out of curiosity after I got married, but never felt any compulsion to continue. But, when I was probably 13 or 14, I remember having a conversation with my older sister in which i told her that it didn't seem fair that girls got to wear makeup to improve on their natural features, but guy were stuck with whatever they had and no chance to improve on his features. The only thing my sister said is "Don't EVER think about wearing makeup!" And that was that.
I think in my twenties i did try some of my wife's mascara once and ended up leaving some residue. I had to make up a story about getting something on my face at work and she bought it.
Fast forward to the last couple of months. i bought some mascara and just put it on one morning after my shower. Since that day I've been wearing mascara almost daily and have been out running errands. I doubt most would notice or care, but my wife has picked up on it pretty much every time I've worn it. She's been civil about it and has come to just accept it. She does warn me if she sees it smeared. I changed to waterproof (at her suggestion) and she doesn't mention smears.
Within the last week, I've experimented with eyeshadow. I picked a color that was too dark and my wife was not impressed. i finally just asked her if she had any eyeshadow palettes that might work for me. She found one with a color that barely shows, if at all, but it still feels good to have it on. But, I had to get out to the grocery store tonight and decided to up my game by adding a little darker shadow. It wasn't over the top, but it was fairly obvious up close in grocery store lighting. I also was wearing women's skinny jeans and a visible sterling ankle bracelet with my sunglasses on top of my head to keep my almost waist-length hair out of my face.
Wouldn't you know it, I ran into a young couple from our church at the grocery store and ended up talking to them for 15-30 minutes and, dodging all the other shoppers, I ended up within two or three feet of one or the other of the couple several times. There is NO way that they didn't notice that I had on eyeshadow and mascara. Fortunately, the couple were probably one of the most accepting people I know and, although they might have discussed the makeup after we went our ways, I feel that they are both very respectful.
Anyway, bottom line is that someone other than my wife has seen me in some fairly obvious makeup and I didn't freak. Sure, I was a little uncomfortable, but the conversation was easy and natural. I take it as another win...
