“A girl I’ve texted, who seemed interested, has now canceled dates twice—once saying she had to work late, and once that she had to go home because her dad was sick. Should I keep pursuing her or let it go? I don’t want to come across as desperate…”

Aw, buddy, it sounds like she’s not interested. But she could also have a demanding job and a sick dad, so all hope is not lost!
Let’s say, on the bright side, that her dad is supersick. I’d suggest giving her a call. When she doesn’t pick up (because she’s either in the hospital with her dying dad or she’s just not that into you), leave a message telling her you hope everything is OK and that you think she’s great and would love to see her (after her dad gets better or dies). Maybe don’t mention her dad, but do reach out. 

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I know this sounds like I’m teasing you, and I am, but because I think there’s too much hesitancy on all of our parts as far as text etiquette goes. Honestly, you have nothing to lose by calling or texting or even e-mailing someone you really like—it’ll show her you care. Worst-case scenario, it may read as slightly desperate, but you are desperate—I mean, you’re writing us about it, right? So just own it!

Then leave it at that. If she doesn’t respond, you’ll know she’s not feeling it and you’ll be able to move on.

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