I have always said it never hurts to ask (just ask my husband). I can’t tell you how many times I have gotten upgrades, free things, etc. just because I asked. I am mentioning this because in my last post I wrote about getting a credit card annual fee waived. I know most people aren’t active duty so I say just ask.
Next time you are at a hotel ask for an amenity or something you don’t normally rate. I’m not saying to lie, but if you’re celebrating anything mention it. One time I was at the Hyatt Chesapeake and we got free s’more kits – next time we didn’t (said it wasn’t part of package) – I “complained” and they gave them to me. If you are flying and it isn’t a big hurry – volunteer to get bumped, I have heard people get amazing financial incentives to volunteer in some instances. Little harder with kids but it might just be another flight 2 hours later – watch a movie on Netflix for that 😀.