I was at a coffee shop yesterday morning and saw the cutest guy. We exchanged some niceties, but did not formally introduce ourselves. I have thought about him since and regret not being more forward in introducing myself. He was wearing a track jacket from the local high school (and obviously was not high school age) so on a whim, I looked up to see if maybe he was a coach at the school. It took about a minute online to figure out his name and that he’s the Track coach at the high school. I was thinking about emailing him to say I thought he was cute, and if he is single ask if he wanted to have coffee or a drink sometime. This is not something I would normally do (i.e. i have never done it!) so I’m leary. I don’t want him to think I am a total stalker. I’m not. I am a very established professional and am by no means desperate. But I’m telling you, that smile was killer 🙂 Thoughts on how to, or how NOT to, proceed?