Didn't know there was a .DATING tld. Anyway as a keywdord the -ing form sucks, and as a TLD it sucks even more. IMO of course. Something like NYC.dating might (a big MIGHT) hold some value but that's about it. Sorry. IMO.,
And don't get me wrong. The domain doesn't look bad. It's actually quite appealing to my eye. Because I look at domains every day, all day. But in terms of (liquid) value, new TLDs hold hardly any value (yup, there are exceptions).
Go ahead, play with new TLDs, a lot of crazy deals out there, but appraising something like Ottawa.Dating is just not possible IMO.
If someone would approach me with $XXX offer, I'd take it. Ottawa isn't exactly the dating city of the world (no, didn't look into it closely.)
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P.s. We're all mates.