The Wednesday Wellness threads are meant to encourage users to ask for and provide advice and motivation to improve their lives. It isn't intended as a 'containment thread' and any content which could go here could instead be posted in its own thread. You could post:
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Requests for advice and / or encouragement. On basically any topic and for any scale of problem.
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Updates to let us know how you are doing. This provides valuable feedback on past advice / encouragement and will hopefully make people feel a little more motivated to follow through. If you want to be reminded to post your update, see the post titled 'update reminders', below.
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Advice. This can be in response to a request for advice or just something that you think could be generally useful for many people here.
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Encouragement. Probably best directed at specific users, but if you feel like just encouraging people in general I don't think anyone is going to object. I don't think I really need to say this, but just to be clear; encouragement should have a generally positive tone and not shame people (if people feel that shame might be an effective tool for motivating people, please discuss this so we can form a group consensus on how to use it rather than just trying it).
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I'm married and have been out of the dating pool for over a decade now, so as many grains of salt as needed, but I see a few things that I consider mistakes:
First, there's no need to frame the situation as a date. You can just say that you want to go out for dinner, or go for a hike, or go to [cool local thing that's happening]. If things go well, you can always suggest grabbing some drinks, then it's pretty obviously a date, and that'll go wherever it'll go. If not, well, you can both play it off like it was never anything more than hanging out with your buddy anyway, so no harm done.
The flattery isn't necessary and probably doesn't help. It may well not hurt either, but it does make some women feel uncomfortable. The fact that you want to hang out with her already pretty clearly informs her that you find her attractive and think she would be fun to hang out with.
Not to go full PUA, but I think you're just too damned nice in the message. The level of niceness gives off a bit of an air of desperation, even if it's not really there. I think men are better off with some degree of carefree nonchalance or making it seem like it should be exciting to hang out with them rather than framing it as though it would kind of be a favor and would be potentially embarrassing if she didn't want to go. Try something shorter, along the lines of, "hey, I'm headed to the concert on the square Thursday night and maybe out for drinks after, want to join?". Framed that way, you're already doing something, it's going to be fun, and if she just doesn't want to she can opt out without actually saying that she doesn't want to go on a date.
Thanks for the feedback. Re: The first bullet, those sorts of “dates that aren’t dates” are how I used to approach things and my experience was that it’s a good way to make friends. So I started trying to be more direct.
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