Romantic Male Box: Self Esteem Edition

Over the weekend, after the afternoon of video games with Smoothie, I decided I had had enough of (literally) fun and games, and maybe it was time to look into meeting a fellow close to my own age. So on Sunday I responded to two Craigslist ads, one from a man 50 years old and one from a man 49 years old.

The 50-year-old responded right away. Italian, divorced with 4 kids. 4 kids! He sent me a photo of himself with his 25-year-old son. The son looked really yummy, but I digress.... I sent my photo and....he never responded. Once again, a stranger was there to remind me that I am not, in true fact, Angelina Jolie. When I informed Smoothie of this exchange, he was angry and said "You need to write back and tell him what a fuckin' douchebag he is". But I didn't. Why bother.

The 49-year-old guy seems quite sharp and nice. Divorced, with one son. At least that is a reasonable number of children. After a few emails, I suggested we exchange pictures to get that out of the way quickly. Why waste time?

Oddly enough, he was reluctant. If his first reply he said he would send one and added: "If you should suddenly go incommunicado after that, like someone who has fallen off the face of the planet, I'll take the hint." And I thought I was insecure!

In the follow-up email he did indeed attach a couple of photos and said: "If I don't hear back, then message received loud and clear." Is that sad or what? Is he playing the pity card? I asked Smoothie what he thought. His words of wisdom: "He's just like me. His self esteem is in the toilet. He knows you're not going to answer."

So, what did he look like? Let us say he is a hybrid of two celebrities: Wallace Shawn and the Lucky Charms leprechaun.

Which is not my type. At all.

At this stage in my life, do I have the right to judge? I'm not sure. But not being a heartless beeoitch I sent my photo in return (a particularly blimpish photo), with a non-commital comment. Smoothie says this was a terrible idea because any response with a photo is a positive response, and if I am not interested I should've just ended it and not give the guy any hope. But I don't like to be mean. Should I have not answered? Or simply said sorry, I'm not interested as you will always be after me Lucky Charms? (What I am really hoping is that he'll take one look at my picture and think "I can do so much better than her" and that will end it. Please reject me, Mr. Shawn the Leprechaun.)

This dating shit is hard. I think I will stick to playing Command & Conquer with Smoothie and arguing about fingerling potatoes with Fancy Feast. Better the devils I know.