Datin’ Without Hatin’ — Dating Advice Column, Debut Edition!

A number of people have asked me to write up some posts about dating advice. Well actually, some have asked me to write a book on it, but would settle for some posts in the meantime.



Since my own love life is nothing but grand epic tragedy of Shakespearean proportions, I find this notion amusing. But people come to me with questions a lot, and find that I’m generally a good resource for advice, because I do have to admit, what I do have going for me other than tragedy is that a) I’ve had a number of very strong, meaningful relationships with genuine connection and exceptional communication, and b) no one I’ve dated has, to my knowledge, come out of the experience hating my guts; they all wanted to be friends afterward. So my area of limited expertise is probably something like, “How to date without making anyone hate you.” Hence the catchy title of this column.


Note that most of the questions I’m asked and most of the experience I have is in regard to dating for the sake of a long-term monogamous relationship. I’m not a casual dater, and neither are most of the people in my social circles, so this column will likely reflect that. But I have on occasion been a sounding board for other sorts of dating, so if your questions go along those lines, I will certainly endeavor to answer them to the best of my ability.


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I decided to kick things off with a simple Q & A post, sent in by an anonymous woman in need of some advice recently. Behold the following exchange of ideas:


I have a second date next week. I have a sneaking suspicion that this will not work out between us.
How do I tell him that?


Well, in my experience, there’s no way that it won’t be at least a little awkward, but not too bad if you stick with something like, “Look, I think you’re a really nice guy, but I don’t really see this going anywhere. I’d be glad to keep an eye out for girls who I think would be a better fit?” Bonus points if you have someone in mind and offer to check if she’s available.

Also, maybe at least let the date play out in case he pleasantly surprises you the second time. Unless you have really hardcore reasons why the first date was enough (in which case, it may be better in the future if you don’t accept a second date).

I definitely do recommend breaking things off in person, if it comes to that, mostly because I’ve been the listening ear to a lot of guys who’ve had things ended over text or in other impersonal ways and they’ve been pretty hurt by it.

I’m definitely letting the second date play out. That’s what the second date is for (at least this time). Good to know to do it in person though. I guess I’ll have to decide then if I should do it right after the date or do it another time (if at all).

When I was on a date with a guy I knew I didn’t want to see again, at the very end he accidentally gave me an opening just before he dropped me off, by saying, “So I’ll call you?” And then I got to be all, “Look, you’re a nice guy, but etc, etc.” So if you’re sure by the end of the date, it’s fair to say something at the tail end just to close the book.

If you’re not sure at that point, but become sure after the date has ended, well, then if he contacts you afterward, it might be better to tell him over the phone that you don’t want a third date so that he doesn’t go through the trouble of planning one, with misplaced expectations.

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And there you have it: how to politely reject someone straightforwardly but hopefully with a minimum of hard feelings. In the words of Wil Wheaton, don’t be a dick.

Got questions of your own that you’d like me to take a stab at? Stick ’em in the comments, tweet at me @FloatingSpirals, or if you’d prefer more privacy/anonymity, email them to me at smautomotive00@gmail.com!



Agree? Disagree? Like my thinky thoughts? You can commission more of them via my GoFundMe campaign — http://www.gofundme.com/sm-automotive — or subscribe on the sidebar, and thanks for reading! You can also buy me tools from this Wishlist but really I just like money.


One thought on “Datin’ Without Hatin’ — Dating Advice Column, Debut Edition!”

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