Should I send a gift to this person?

December 20, 2010 5:32 AM

Would you ever send someone an anonymous gift - particularly if you haven't had a good relationship with them?

I have never really sent anyone an anonymous gift before but I like the idea of it. This wouldn't be a totally anonymous gift because I think they will know it's from me but I wouldn't be putting my name or address on it either.

The person I'm thinking about sending it to is one of my former managers - we've had a tempestuous relationship and I don't know if we'll ever work together again, but I would like to should the opportunity arise.

However, I don't want to make a big song and dance out of this gift - I just want them to get it and interpret it however they wish. On the one hand I don't see how it could make anything worse than it already is, on the other hand, it is a weird thing to do when you've not had a great relationship with one another.

Do you think I should send an anonymous gift to this person?

posted by mleigh to human relations (22 answers total)

I wouldn't send anyone a gift if I had a tempestuous relationship with unless I loved them. I've better ways to spend my money.

You say you want them to get it and interpret it however they wish...but if you give it anonymously, how can they interpret anything? "Oh, here's some perfume." or "Oh, here's a severed horse head and some black roses. There's no card. Oh well."

It just seems a little weird.
posted by inturnaround at 5:35 AM on December 20, 2010 [2 favorites]

Hmm... not really. As you say, it's a weird thing to do. Introducing an additional layer of awkwardness into your relationship with someone isn't going to improve your chances of working with this person again.
posted by le morte de bea arthur at 5:37 AM on December 20, 2010 [1 favorite]

No. Put your name on the gift with a nice note so don't leave room for open interpretation--especially if you want to work with/for this person sometime in the future.
posted by sandra194 at 5:39 AM on December 20, 2010 [1 favorite]

If, as you say, your former manager will be able to tell that it was from you, the anonymity just adds another layer of confusion and awkwardness to the whole situation.

I don't really understand from your question why you are getting this person a gift at all. Because you may work with them some day? Why not meet for coffee and repair your relationship?

If you're looking to inject a little drama, or put a little hitch in this person's holiday, then I think the anonymous gift is the perfect way to go about it.
posted by Think_Long at 5:43 AM on December 20, 2010 [5 favorites]

I feel like there is probably much more to this story than you're telling us. But from what you've said, it seems like a weird and sort of unprofessional thing to do.
posted by craichead at 5:45 AM on December 20, 2010 [2 favorites]

If you're looking to inject a little drama, or put a little hitch in this person's holiday, then I think the anonymous gift is the perfect way to go about it.

I used to work with a woman with a really irrational temper, who made my job a living hell until I left the company. She once returned from lunch and left a cupcake on my desk for me.

This was five years ago, and it still makes me feel weird.

I agree with Think_Long: if this is a relationship you actually want to improve, meet face-to-face and make nice.
posted by jaynewould at 5:48 AM on December 20, 2010 [2 favorites]

I sent my secret Quonsar an anonymous birthday present this year (she had posted her amazon wishlist to elfster and it included a birthday, which I took note of). This is obviously a very different kind of anonymous gift, but nonetheless, I put a fair bit of work into getting the gift and I found it disappointing to never know if it was received, if she liked it, etc. And so I note that anonymous gifts are a bit of a letdown from the giver's point of view. You say he can interpret it however he wishes, but won't you find it awkward to never know how he interpreted it?

Just put your name on it. You say you don't want to make a big deal of it, but under your circumstances making it quasi-anonymous seems to make it a bigger deal than just attaching a card.
posted by If only I had a penguin... at 5:50 AM on December 20, 2010 [2 favorites]

Another vote for "really weird". If you have something to say to this person, say it. Want to improve your relationship with them? Then make plans to meet for coffee and have a discussion. Take the lead in making things better. Be an adult about this, not a sneaky little kid trying to curry favor in an anonymous Eddie Haskell sort of way.

From the information you've given us, this sounds like a bizarre passive-aggressive move. Be straightforward in your actions and in your words. I really do not think a not-so-anonymous gift will improve your relationship with this person. If I got something like this, I would be very put off.
posted by Kangaroo at 6:00 AM on December 20, 2010

That sounds weird to me; if I was the recipient I think I'd be less than delighted. Be a grown up and put your name on it, unless you already have a relationship where an anonymous gift would be welcomed and appreciated.
posted by Forktine at 6:00 AM on December 20, 2010

You say you want the recipient to "interpret it how they wish," but allow me to suggest that the range of "how they wish" includes such things as "wow, mleigh is a stalkerish weirdo." Also allow me to suggest that if you can't see how this could make anything worse than it already is, you haven't spent enough time thinking about what your real motivation is, how likely it is that this gesture will accomplish that, and the likelihood that it will instead accomplish the exact opposite.

In other words, ask yourself: what am I trying to accomplish here? You've stated one thing that you're hoping not to accomplish (making a big song and dance out of it), but there are probably better ways to accomplish your goal here that neither make a big song and dance nor send off freaky vibes.
posted by SomeTrickPony at 6:03 AM on December 20, 2010

I have received a few anonymous gifts from people with whom I had a tempestuous relationship. "Anonymous" in the sense that they didn't label it with their name, but I knew who it was from. (Now that I think about it, it's pretty weird that this has happened to me more than once.) Every time, I felt like I was being emotionally manipulated. It really reduced any amiable feelings I still had toward the person, because I resented them for not being direct with me. A small gift with an honest note -- or even better, just an honest note -- would have been much more welcome.
posted by neushoorn at 6:19 AM on December 20, 2010 [10 favorites]

Yup, weird. I'd be put off. And, if you expect that the recipient will know where it came from, and you anticipate some sort of benefit from the gesture, why be anonymous in the first place?
posted by GenjiandProust at 6:20 AM on December 20, 2010

I got an anonymous gift once, liked it, then was gutted when I realised who it was from (or rather not from!). Although I was young so I guess I slightly enjoyed the mini drama.

If it was now, I'd just be creeped out and a little annoyed.
posted by greenish at 6:44 AM on December 20, 2010

Don't make it anonymous, and use a note to defuse any weirdness or impropriety.

"I have no real reason for sending you this, I just thought you'd like it. I enjoyed working with you, even the stressful parts, and learned a lot. Best of luck in 2011!"

Or something like that. Tone = business-friendly.
posted by rokusan at 6:53 AM on December 20, 2010 [3 favorites]

My sister received an anonymous dehydrated frog in the mail when she was in high school. She had a guess who might have sent it but never found out for sure. It didn't improve her relationship with anyone.
posted by alms at 7:08 AM on December 20, 2010 [4 favorites]

I assume that the gift itself is supposed to be some kind of coy "message" gift, right? As in, the recipient should piece it together through some kind of winking "a-ha"?

Skip it. If you want to reach out to this person, reach out to him/her. If you want to enact some kind of fantasy drama, it's so not worth it.
posted by mkultra at 7:09 AM on December 20, 2010

I don't want to make a big song and dance out of this gift

Then don't do something overdramatic like making it anonymous. An explanation of a surprising gift isn't the same as self-aggrandizement. Include a note that explains why you're sending the gift and gives some clue as to what kind of reaction you're hoping for (i.e., forgiveness, friendship, etc.):

Dear [Former Manager],

[I owe you an apology / I'd like for us to be on better terms / We have our differences, but I really admire your talent / whatever]. I saw this [gift item] the other day and thought of you. Would you like to get coffee sometime in the new year?

Yours,

mleigh
posted by Meg_Murry at 7:12 AM on December 20, 2010

If I received an anonymous gift, I would be freaked out. In a world with exes, rapists, criminals, and creepers, I would be mostly concerned that this was a sign someone had ill-will towards me, and given that you don't know what weird traumatic events have happened to this person (who knows if they have restraining orders out against someone? Maybe they have family they have cut off contact from. Maybe they put someone in jail? You don't know) you could really ruin their holiday.

Unless that is your endgame...
posted by jenlovesponies at 8:49 AM on December 20, 2010

Don't do it if you're trying to endear yourself to this person. I've received anonymous gifts before, from someone I didn't have a good relationship with. I found it unsettling and sort of hostile. It just felt like a power thing where the giver has all the information and the receiver is just supposed to wonder.
posted by violette at 9:51 AM on December 20, 2010

>>I just want them to get it and interpret it however they wish.

So... you want to mess with this person? I can't advise fucking with a person's head just for the hell of it.

The fact that you think they might be able to figure out it's from you adds an extra level of weird, too. And you want to be able to work with this person in the future? That makes it even more of a bad idea.
posted by J. Wilson at 12:37 PM on December 20, 2010

What? No. It would be weird to send even if you put your name on it. Inappropriate gifts (in that you had no good reason to give it to them, and there's no reciprocal social context for it) can be even weirder than anonymous gifts. But not as bad as an anonymous gift she figures out is from you. If what you want is to repair your working relationship and network, then ask her out for coffee to talk about professional stuff.
posted by yarly at 12:56 PM on December 20, 2010

Thank you for all the votes for weird!

For context - this was a small firm and we are both rather old-fashioned creative types (as opposed to your cutting edge creative types). After finding out about some major personal drama in my life, he made significant efforts to repair our relationship, all of which were thwarted by me. I have realised he himself has had some personal drama going on, and my response to him would not have helped. The gift I was going to give is something I've had for a while now, I carry it around in my bag - it's akin to an inspirational/motivational card, and costs about $10. My intentions were not to manipulate him, but rather to show him that his efforts were appreciated.

As you've all said, it would be really weird without context, so if I do send it to him, I will explain to him why I'm sending it - or I may even skip the gift altogether and just write the letter. The biggest problem has been a lack of open communication so I should probably not add any more to that!
posted by mleigh at 1:46 PM on December 20, 2010 [1 favorite]