Q: Dear Dating Girl-
So I have this loooong standing off and on crush (about 5 years now) with a guy who has been my boss for the last 2 (although my position has changed so he is no longer my direct supervisor). We met through a volunteer program, stayed in touch afterward and he hired me when I was looking for a job a while back. He's a great guy and I remember hitting it off with him right away (through the phone no less) when we first met. The down side is he's a bit older and not the most attractive, but he's amazing and being with him, whether its for work or fun, is just good (I've pretty much been told by a friend or two that I'm in love with him which I hate because we've never dated. Argh I'm a loser!). So anyway, I'm trying to figure out whether its worth making the first move...I mean we have known each other for a long time and he's never made a move and he is a committment phobe. We are like the best friends who know everything about each other but have never dated and I'm the girl in love while he's the guy without a clue, this it terribly cliche. So what should I do? Got any advice on how to make my feelings known without out right saying it? Or should I just say it and let the chips fall where they may?
A: You have to make the joke about it so he hears it but you’re not too vulnerable. Say, “Too bad we’re just friends; you’d make such a good boyfriend!” Then see what he says. He may just laugh it off and never think of it again but he may chime in with something. Just be prepared to answer back if he opens the door. So if he says, “Yeah, we could be good…,” then you have to say, “If I were more adventurous, I’d lean in and kiss you right now...” Or, “You should just ask me out already!”
Let me know what you think!
LTM,
DG
Moosejaw.com
The Dating Girl and all of its related content are meant for entertainment purposes only and do not contain professional or other advice. The views, opinions, points of view and comments expressed by the Dating Girl are not intended to provide professional or other advice and are not those of Moosejaw Mountaineering and Backcountry Travel, Inc.
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