Dating 101: Men, Makeup & Nerves

I had a date last night with a man I met on He is 52, 5’10”, dark hair, blue eyes, works in finance, divorced, two adult children, and a great sense of humor. We spoke on the phone twice and our conversations were short but fun.  We decided to meet for a drink. He offered to pick me up, which was sweet, but that is never happening. I don’t let men pick me up for a first date. Nobody needs to know where I live thank you very much.

So I got dressed in a pretty black sweater with jeans and high-heeled boots. My hair looked fabulous and I wore my standard makeup of mascara and lipstick. I am very minimal in the makeup department and prefer a more natural look. Unless of course I am getting my makeup done for my BiteSizeTV show, in which case I am all about fake eyelashes and a few more layers of paint. I looked pretty and fresh faced for my drink date.

I got to the restaurant on time and he was there already. Nice. He was waiting for me in the entrance, which I should mention is a little more lit than the bar.  As he said hello and flashed his pearly whites, I immediately went in for a hug so I would have a second to gather my composure and make sure I wiped the panicked look of surprise off my face. This lovely man was wearing more makeup than I was. It was both shocking and hilarious.

I cannot imagine how he thought it looked good or for one second it was subtle. He was wearing black eyeliner, mascara, blush, and I’m guessing a strawberry flavored lip gloss, which I got a sniff of as he kissed me on the cheek. As we walked to the table he had scoped out for us at the bar, I was a little embarrassed and wondered what people would think. I braced myself for the waitress to come over and wished it was a little darker.

We settled into our chairs and I got a good look for the first time. My date had done a line of black eyeliner along the top of his lid, and a smaller line along the bottom. He had on mascara, contouring blush along his cheekbones, and the hint of lip glass. His eyes were a lovely shade of blue so I understand how he thought the eye makeup would make the color pop, but no. As for his lips, unless it is Chapstick, I do not get the lip gloss.

He was a nice enough man, as funny in person as he was on the phone, but I just could not get past his makeup. I wanted so much to ask him about it but just couldn’t. As we spoke I realized he was not an avant-garde artsy type who was expressing himself, but rather a man who was dealing with getting older, dating after divorce, and trying to make himself look young. By the time we were done I figured he was probably closer to 62 than 52.

I always get nervous before a date. I panic a little, get a stomachache, curse the fate of being single at 47, and pray I will get home safely and not encounter someone dangerous.  It is nerve-racking to take a chance and put yourself out there. While I often wonder why I bother to keep trying, I have faith that love will be found and so I date. There have been hits and misses but since I’m single, the misses clearly outweigh hits.

My date last night got me to thinking about how men feel about dating. This man was nervous and somewhat desperate. I truly think he was wearing the makeup in an attempt to look as young as he wants people to think he is. Had he not worn the makeup, and said he was in his 60’s, he would have much better luck. This blog is about the makeup so I won’t talk about the hair color, which was rather shoe polish gothic in its darkness.

I suppose it could be possible he is a diehard Twilight fan and was going for a vampire look. Perhaps he plays in a band at night and was meeting me for a drink before his gig.  There are a lot so reasons he might have opted to come in full makeup, but I really think it was just a man feeling the same nerves that women feel to be dating later in life. Maybe the key to calming down dating nerves is to know that the man is feeling the same way.

I won’t go out with this man again. Bless him. I am however grateful for the date and walked away with a giggle at his makeup, but also a smile in my heart. Everyone is on their own path and the road to love is a bumpy one. I hope this man will meet a woman who likes her men in makeup. There is someone for everyone and I believe each bad dates gets me closer to a good one.  Perhaps that is naïve, but it allows me to keep the faith.