Shopping for gifts. Some hate it, some spend months searching for the perfect thing. Others give cash, because who has time for shopping? If your recipient is any kind of decent human being, it's truly the thought that counts - and cash is always king. But sometimes, giving a fistful of dollars can come across as rude, presumptuous or otherwise inappropriate.
The big occasions are easy - Christmas, birthdays, and especially weddings, where you can just choose something off the registry and rest assured it will be perfect. But what about those weird occasions where a gift feels appropriate, but danged if you know what kind? Housewarming, dinner parties, house/pet sitter gifts, etc. These situations can be tricky. But like any occasion, these kinds of gifts are best dealt with by thinking of the recipient first.
A potted plant is the standby gift here, meant to brighten up the new home. It's nice, and it works - but other options may be more helpful. Is the place a fixer-upper? Try a gift card to a home improvement store. Are you giving the gift on moving day? Bring a hot meal, which they won't be able to cook for themselves because nobody knows where the pots and pans are. Be sure to bring paper plates and disposable cutlery. By thinking outside the flowerpot, you end up giving a truly useful gift and looking like a lifesaver.
Hostess gifts are meant to be a way of saying "thank you" before the meal/party/whatever has begun. There are some rules here: first, never bring food unless you were specifically requested to do so. You don't want your hostess to feel pressured to serve a dish that may not jibe with the rest of the meal. Second, never bring a bouquet - your hostess doesn't have time to look for a vase, trim stems, and all that garbage. She's busy greeting guests and getting drinks out.
That said, Artisanal food gifts are fine, as long as you make it clear that the gift is to be enjoyed at a later date. Gift baskets make this apparent. Flowers are also okay if they are already in a vase, and all your hostess has to do is put them on the mantle. Wine is a nice gift, as are candles and gourmet candy - but make it clear that the gift is for her, not the party. Also, help with the dishes.
If your house sitter or pet sitter is a professional who you hired just to do the job, no gift is necessary. If you return to a freshly-cleaned home, a fantastically happy dog, or it appears she has gone above and beyond the call of duty, a cash tip is appropriate. Otherwise, she's being paid for the job.
If the sitter is a friend, neighbor or family member doing you a favor, a better gesture is in order. A souvenir from your trip is nice, but not a tacky T-shirt or mug. Choose something that place is famous for. A Venetian glass vase, a Venezuelan leather tote, a hand-woven Mexican hammock, etc. - these gifts tell the story of where you were, and their imported counterparts are generally way more expensive.
If you were only away for a weekend, you can stop there. Extended vacations call for more thank you's. Take her out to dinner, or give her a gift card to her favorite restaurant (make it enough that it will actually pay for a meal for two). Of course, you should also offer to return the favor the next time she goes on vacation.
Gift-giving is an art, and giving a gift that will be used (instead of just taking up space and needing dusting) makes the recipient feel like she's received something of actual value. Now if only we could think this way for all gift occasions (ugly Christmas sweater anyone?).