Q: Dear Ava. I’m a labourer working on construction sites most of the time in a big city. I consider most of the guys I work with as neanderthals. The older ones anyways. I’m twenty-four. The guys are always whistling and throwing catcalls at girls half their age, and it’s kinda gross. The women’s responses are usually that of total disdain or they tell the guy to fuck off. I consider myself good looking and don’t participate in this sort of thing. Anyway, to get to my question. There’s a coffee shop I frequent almost daily to pick up a tray for the boys and there’s this beautiful woman who works there that I can’t stop thinking about. Thing is, she’s probably late-thirties or maybe older. She isn’t wearing a wedding ring and I’m sure she’s flirting with me. I always seem to say something to make her laugh and she makes crazy eye contact with me. She has amazing green eyes. And when she hands my change back her fingers seem to linger while touching mine, although I might be imagining this. How do I know for sure if she’s interested and then what do I do. I’m a bit shy if that isn’t obvious. -Jesse in Pennsylvania
A: Hi Jesse. A couple of things. If you consider yourself good looking and you know how to make a woman laugh you can’t be that shy. You’re not giving yourself enough credit. Making a cougar laugh with you (not at you) isn’t always the easiest thing, but it is a sure sign that some kind of chemistry is brewing. If I want to send a message to a younger man that I like, I’ll often use eye contact to grab and hold his attention. I’d say the shared laughter, eye contact, and the prolonged hand touching are all signs that this woman is flirting and interested. Don’t forget, she’s at work and may feel uncomfortable about making any further kind of play in this environment. Older women love confidence and even if you have to fake it (a bit) til you make it – do it! We want that younger man to make the first move – believe me it will be rewarded later. I’ll give you two suggestions. Write your phone number and a short note (e.g., maybe we can go for a drink sometime?), or I’ll be at (such and such a bar/resto) tonight around 8 if you want to stop by for a drink). Giving your number gives her the control, but still shows your not afraid to lead. By the by, I’ve always had a thing for construction workers; something about men that work with their hands, especially the young ones. Prrr. Best of luck, Jesse.
Cubs: Have any first moves you want to share?
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