1. Dan

    I’m leaving my job in a few weeks for another opportunity and I want to send gifts to my boss who has been exceptionally supportive of the change. Knowing that you shouldn’t gift a current boss, I’ll wait until I’m in my new job and send him a bottle with a thank you note.

    The question is, which bottle, and is a bottle OK? I know he isn’t a teetotaler because at one business lunch he ordered sangria for the team. I’m not sure if the usual etiquette of the $25 limit holds in this case since he’s technically now a business associate or former colleague, and I’ve received dozens of expensive bottles from clients in the past. I kind of want to just send a Macallan 12 and hope that isn’t incorrect.

    • Elizabeth

      That sounds like a lovely gesture, and not at all one that seems out of the bounds of propriety. It would be nice if you could ascertain in advance what kind of liquor he preferred. (You wouldn’t want to give bourbon to a dedicated vodka drinker, for instance.) But if you can’t, then the ‘spirit’ of the scotch as something sort of masculine and luxurious seems quite right.

    • Jerry

      In this case you can give the gift to your current boss as you’re going to be leaving. (The prohibition on giving gifts of non-nominal value to your boss comes from the principle that you don’t want to be seen as brown nosing. Twenty-five dollars is not a hard and fast rule either.)

      Feel free to spend an appropriate amount on a gift that you think he’ll like. If you feel comfortable with the $40 bottle of scotch, go for it! And feel free to bring it to his office on the last day. No harm there, either, and you get to see the look on his face when he opens it.

    • Dan

      Thanks, everyone! Much appreciated. Elizabeth — that’s pretty much exactly what I was going for. He’s kind of tight-lipped so no one seems to know what he likes to drink, so I thought the scotch would convey the idea, and if he doesn’t like it he could keep it around for guests or re-gift.

      Thanks again!

  2. Sarah

    Hello. Once a month I meet an old friend for dinner. Around my birthday, she paid for the dinner and gave me a gift. I have a gift for her and on the day of her birthday I texted her “Happy Birthday” and followed it with “pick a restaurant for Wednesday, as this dinner is in honor of your birthday!” However, now I realize that I don’t want to place her in the awkward position of choosing a restaurant–she may not want to pick something deemed too expensive. But, if I now say “How about we go to Jazzy’s?” to take the pressure off her having to make a decision, I also feel like I’m pushing a restaurant on her. What do I do?

    • Country Girl

      I would just call her. It would be nice to confirm by phone anyway. Then simply ask if there is a special restaurant she’d like to go for her birthday dinner. She either will have a restaurant in mind and be thrilled that you let her pick, or she’ll say she can’t think of a place and then you can step in with a couple of options for her. Either way, you did nothing wrong and it should be a fun night for you both! =)

    • Jody

      What a nice gift — and how thoughtful of you to consider her feelings. Maybe you can send her a followup message along the lines of “in case you’re having trouble deciding on a place, here are some ideas” and then you can give her a range of places to choose from. If there’s a place where you’ve both gone in the past and enjoyed the meal, make sure that place is on the list.

    • Victoria

      Give her a call and say, “have you had a chance to think about which restaurant you’d like? I didn’t mean to put you on the spot!” An awkward moment can always be handled better live than in texting, which has no subtlety about it and is open to misunderstanding.

  3. Shakey!

    We have all had an awkward hand shake or two, most are recoverable.

    What do you do when the other person you are shaking hands with lingers too long and continues to awkwardly shake, even when you lighten your grip as if releasing?

    -Shaken To Death!

    • Zakafury

      I say just put up with it. Pull your arm back from the elbow after a couple of pumps. I guess one last squeeze and release might get the point across.

      As someone who cares about etiquette, you can just be sure you’re not the one being overbearing and excuse the ignorance of others as best you can.

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