Should I click "send"?

June 4, 2006 9:58 PM

Should I click "send"?

I've written a slightly angsty letter to a (formerly very close) friend, explaining the many insecurities that led me to turn him down romantically several months ago. Should I send it, considering he's moved on with his life?

Previous threads here have advised to only do so if you want a relationship, but while I do love and care for him deeply and can picture it working... my insecurities remain, so on the off chance he's actually still willing they'd probably just rear their ugly hydra-like heads again. Plus there's a chance he'd react with anger, which would really only make my insecurities worse.

Yes, I probably need therapy, but have to make this decision very soon. MetaFilter, could you give me a push?

posted by anonymous to human relations (56 comments total)

As someone... experienced in these matters: No, you should not send it.
posted by dobbs at 10:04 PM on June 4, 2006

No.
posted by Mr. Six at 10:07 PM on June 4, 2006

I second dobbs's advice. I suspect it was somewhat therapeutic for you to write the letter, and that's great. From your description of the situation, actually sending it sounds like it would in all probability create more problems than it solves.
posted by cerebus19 at 10:10 PM on June 4, 2006

no.
posted by odinsdream at 10:12 PM on June 4, 2006

No.
posted by cribcage at 10:13 PM on June 4, 2006

No.
posted by about_time at 10:17 PM on June 4, 2006

If you've been picturing it working ... you want it to work, right? Then you need to shelve that letter and write another one, less angsty, explaining a bit what went wrong and more about what you want to go right.

Then sleep on it, and decide about sending that one, tomorrow.
posted by bonaldi at 10:21 PM on June 4, 2006

Do not send it. I would love to be able to slap my younger self around with a wet noodle with regards to sending angsty letters. Just say no.
posted by Justinian at 10:29 PM on June 4, 2006

What the hell -- maybe.

Put it aside for a week. If all this happened months ago, what's another week? Then, after a week, try to read it as if you found it in the street. If you didn't know you, what conclusions would you draw from this letter alone about your motives?

I am guessing you would find it difficult to put it aside for a week, that you are spending a lot of mental energy on this guy and what might have been these days. That might be because you made a terrible mistake with him that could possibly be fixed, or it could be because there is something else stressing you out in your life that you don't want to think about.

If, after a week, you find that your letter passes the test --
Send. Why not?

If, after a week, your letter seems hysterical or manipulative or whatever to you --
Don't send.

And especially, if you just cannot bring yourself to wait a week --
Don't send.
posted by Methylviolet at 10:34 PM on June 4, 2006

I can't see the point in people saying "no" without backing up their opinion in any way.

I will therefore say "yes", and explain the rationales: first, it will probably make both your lives just that little bit more interesting than if you don't (interesting, perhaps, in the Chinese sense), and second, it just might help the situation. If it doesn't help, then at least you won't die wondering.

(I could be playing devil's advocate here, just because everybody seems so opposed to the idea)
posted by UbuRoivas at 10:49 PM on June 4, 2006

Several months ago? You'd just be sending that email to make yourself feel better. Lame move.
posted by xmutex at 10:49 PM on June 4, 2006

I'll qualify my "no" answer: Move on. Seriously. You'll be happier after you move on with your life.
posted by Mr. Six at 10:51 PM on June 4, 2006

What does "moved on with his life" mean?

Just that he appears to be over you, or has he got a new relationship? If the latter, definitely not.

Post the letter here instead. Unless he reads Ask.
posted by AmbroseChapel at 10:58 PM on June 4, 2006

I agree with Methylviolet. If the letter seems right in a week, go ahead and send it; if it doesn't, you just averted a bigger problem.
posted by Penks at 11:09 PM on June 4, 2006

NO
posted by crypticgeek at 11:12 PM on June 4, 2006

No. If I were him, I'd only be okay with only one of two things from you: 1) if you decide you do want to be in a romantic relationship, go make a move in person; or 2) if you don't want to be in a romantic relationship, leave the guy alone. And sounds like choice #1 may not be a good option if he's already moved on and you're still not sure.
posted by mullacc at 11:18 PM on June 4, 2006

No, don't send it.

If he's moved on with his life, this will probably only bring back the bitterness he felt when you initially turned him down.

If you do send it, be prepared for his reply, which will most likely not be kind.

You missed your chance.

Deal with it.
posted by Afroblanco at 11:25 PM on June 4, 2006

no
posted by crewshell at 11:42 PM on June 4, 2006

I had already gone to bed, but the answer I gave you kept bugging me.

It's not entirely clear from your post, but if your friendship with him is completely lost because of your rejection, then send the letter. You have nothing else to lose there, except probably getting an angry response from him, for which you should be prepared.

But if the friendship can still be salvaged, my previous advice (or rather Methylviolet's) still stands: Wait a week or two.
posted by Penks at 11:43 PM on June 4, 2006

No.

As long as 'moved on' doesn't mean found someone new, there's nothing wrong with trying to start up a relationship, and dealing with your issues when they come up. Or not starting up a relationship because you decide that you want to be right with yourself before you pursue someone else. Both happen frequently, they're just part of the broad spectrum of human relationships.

Just don't send a letter! I've got my own share of letters at the bottom of a drawer in my house that I am infinitely glad to not have sent. I've also received one or two such letters, and to be honest they come across as very intense and borderline hysterical.
posted by teem at 11:49 PM on June 4, 2006

I once sent such a letter. Fortunately, the recipient was even more messed up than me, and instead of filing a restraining order, she helped us rekindle our friendship. Unfortunately, the recipient was even more messed up than me. I'm very sympathetic to your position, and I say that as someone who normally disdains to participate in relationship threads. Cheer up, move on, and don't send the letter.
posted by gsteff at 12:42 AM on June 5, 2006

Yes
posted by spork at 1:10 AM on June 5, 2006

I think Methylviolet has got it. I personally wouldn't wig out at receiving such a letter in a similar situation. In fact, I'd probably appreciate it. Do you have any reason to doubt his coping mechanisms?

On the other hand, if you are as insecure as you claim, sending a letter like this is just exposing a flank from which he may well decide to draw blood if he's bitter about the whole thing.

So yeah, wait a week and then decide, as Methylviolet suggested.
posted by Ritchie at 1:23 AM on June 5, 2006

Honey, is that you? If it is, please send the email or I will not otherwise ever know how you truly feel. Working through insecurities are part of what make relationships worthwhile. If I am a true friend, which I profess to be, we can work through this.
posted by |n$eCur3 at 2:10 AM on June 5, 2006

Have you worked out what you are looking for, outcome-wise? In otherwords, once you hit send, will you be waiting for an email along the lines of "I'm so glad you wrote, lets try again?" If you don't get that, how will you feel? How will you feel if the reply is similar to "It was a while ago, I've moved on with my life, get over it because I am totally over you" What if he doesn't reply at all?

These things never have a way of turning out as Hollywood would like us to believe.

Don't send it.
posted by necessitas at 4:09 AM on June 5, 2006

What good can come of it ?
posted by XiBe at 4:27 AM on June 5, 2006

yes.

send it. if you don't, you'll wonder what would have happened for the rest of your life; he'll always feel the rejection without ever knowing his interest was requited.

i'm not saying that sending the letter will automatically make everything happy and wonderful - it's likely to precipitate some difficult conversations, at very least - but at least he'll know, and in the end that may pay off. as for your insecurities, it would be unnatural not to have those - you'll work through them together, if it's meant to be.


in the end, you'll only regret the things you didn't do.
posted by ab3 at 4:44 AM on June 5, 2006

This illuminates an interesting dynamic I've been wondering about in recent days.

1. Question is posed to group.
2. Group is nearly unanimous in answer (in this case, "no")
3. Handwringing ensues.
4. Some chime in with complicated opposite ("yes") answers or even change their answer.
5. Over continuing debate, group answer thus shifts over to other side.

Or perhaps just appears to. The opposition may just be louder or more willing to spend time marshall its rhetorical forces.

I wonder about the "correctness" of the final answer. Whether the first clearhanded answer was really better, before the handwringing clouded the waters (to mix my MetaFores).

It could also just be sour grapes for me being the sole person remaining in opposition to a group decision yesterday :)
posted by intermod at 4:58 AM on June 5, 2006

clearheaded
posted by intermod at 5:01 AM on June 5, 2006

Send it.

I'd like to echo ab3's sentiments (in the end, you'll only regret the things you didn't do.) but with a twist. You always regret the things you didn't do more than the things you did. (~
It's easier to apologize than ask for permission.)

I am of course assuming that moved on doesn't mean married or engaged...

The worst that can happen if you send it is still better than the nothing that will happen if you don't. Doubt and what-if are corrosive.

Anyone else curious about how many of the yesses have unrequited crushes themselves?

Good luck with whatever you choose to do.
posted by KevCed at 5:28 AM on June 5, 2006

No. Absolutely not.
posted by bim at 5:30 AM on June 5, 2006

For goodness sake, just send it. What's the worst that can happen?
posted by reklaw at 5:55 AM on June 5, 2006

No. Give the poor guy a break.
posted by mykl at 5:58 AM on June 5, 2006

What's the worst that can happen?

That the sender can wind up feeling a lot worse. Is that so hard to understand?

Don't send it. Move on.
posted by languagehat at 6:00 AM on June 5, 2006

Writing the letter was probably very good and helpful for you, but I can't see it doing much for him. Don't send it.
posted by JanetLand at 6:09 AM on June 5, 2006

I generally preach the gospel of trying to avoid regret at all costs, and so would normally say "fuck it send it," but I agree with mullacc:

1) if you decide you do want to be in a romantic relationship, go make a move in person; or 2) if you don't want to be in a romantic relationship, leave the guy alone.

If you just want to rekindle the friendship, also do that in person or try sending a cheerier, angst-free email.
posted by CunningLinguist at 6:13 AM on June 5, 2006

Print it. Burn it.
posted by jon_kill at 6:16 AM on June 5, 2006

No. No. No.

Something about email makes emotional content easy to misread. People read conflict into emails meant to have no emotional content at all. Don't ever send anything involving feelings in an email unless they are unquestionably happy nice things.

And this sounds like something two people should say to each other in person if they should say these things at all. If it were me, and that face to face opportunity to talk didn't slap me in the face, I wouldn't force it.

Insecurity clouds reality big time. Let time give each of you perspective. Let yourselves heal without any additional wounds.
posted by dog food sugar at 6:31 AM on June 5, 2006

Rejecting him again, more thoroughly, three months down the line?

Don't do it.
posted by availablelight at 6:40 AM on June 5, 2006

Howdy:

If you are self-identifying this letter as "angsty", I would recommend against sending it. Try reversing your roles: if you received this letter from someone else, how would it hit you? As a genuine attempt to connect, or as a really unnerving emotional dump from someone?

In general, soul-baring letters/emails/notes and the like serve an excellent purpose for the person writing them: they're a way of consolidating very emotional thoughts and getting them out in the open so that you can deal with them.

The receiver, though, may view it as you basically using them for therapy. I'm not saying it can't have a great effect: it's just that, in my experience, it's rare for it to do so. Especially if you want a continuing relationship with the person.

In relationships, soul-baring usually comes later in the relationship, after stuff like "here's what I like, do you like it too" and a few dates and so forth. And, and here's my crucial point, it works best if it's consensual.

This will work best if you can establish a relationship and, in some way, at some point, say "I need to lay a lot of heavy stuff on you", with a corresponding "I am ready for you to lay a lot of heavy stuff on me" from them.

Just my $0.02, from the perspective of having had more than one of these things ruin a relationship in its cradle for me, both on the sending and receiving side.
posted by scrump at 6:55 AM on June 5, 2006

No. Let me explain.

I think necessitas pretty much nailed it up above. You've written this letter expecting (or perhaps hoping) for a specific response from the would-be recipient. I can almost guarantee that's not the response you'll get, just because of the wide range of human emotions and our generally cussed nature. Of all the other responses that you might get, how many will be helpful to either or both of you? If, after some hard-headed consideration, you think it is more likely than not that the outcome will be helpful, send it. But my guess is that the outcome most likely will not be helpful.
posted by adamrice at 7:23 AM on June 5, 2006

This is what I get from your original question: You're sorry for hurting your friend, you're sorry your insecurities came at a cost of your friendship. You've had a couple of months to stew over it, and while the answer is unchanged, you feel he deserves a jusification for why, although you love him deeply, you won't date him.

Now, speaking as some one who has written a very similar letter, and who never sent it: what you really want is to justify your decision to yourself. This is about your head and your heart and your coming to terms with these insecurities that you realize now are keeping you from what you want, something you could even see being good for you.

It was very important for you to write that letter, it is absolutely crucial that you do not send it. Mostly because he already offered to carry your baggage and you refused. Sending that letter will be like throwing your heavy bags at his back and expecting it not to hurt. You say he has moved on, you need to let him do that, and by doing so, also give yourself the space to work this shit in your head out. You've started to unpack those bags, but you are the one that needs to know what's in there.

But, maybe I've completely misread what's going on with you. In that case, I highly reccomend the "Wait" advice. Read over your letter, print it out, and put it in a drawer. Delete it from your draft folder. When you get the urge to send it again, in a week or a month, take it out and READ IT AGAIN. Then, if you think this letter will help him, and isn't just about helping you, then retype it and send it and let the pieces fall where they may. Good luck! You're not the only one who has been there.
posted by nelleish at 8:06 AM on June 5, 2006

No.

I use Google desktop, and occasionally searches pull up letters that felt so good to write at the time that now, looking back on it, I wish I could have back.

I think the last paragraph of nelleish's post is the best option.
posted by 4ster at 8:36 AM on June 5, 2006

Fuck no.
posted by LarryC at 10:10 AM on June 5, 2006

I don't get it... why do people seem to be reading this as if she just wants to explain why she rejected the guy, but not actually get together with him ("the answer is unchanged", "rejecting him again")? That's not how I read it at all. What it actually says is:

"I've written a slightly angsty letter to a (formerly very close) friend, explaining the many insecurities that led me to turn him down romantically several months ago.... I do love and care for him deeply and can picture it working..."

ie. She just turned him down because of insecurities, and wants to explain that, and does want a relationship with him. What she's scared of is that he's moved on and maybe those insecurities will come back again. It's not at all a matter of "I've thought about it, and here's exactly why I rejected you..." -- it's "I've thought about it, and I've realised I only rejected you because of [whatever]... let's try again".

And in those circumstances, I think that sending it is the right course of action.
posted by reklaw at 10:17 AM on June 5, 2006

So basically... "A few months ago, you were interested in me, and I said no. Well, I thought about it alot, really considered what you meant to me, and...well...no."

Is there something positive in this letter? If not, don't send it.
posted by effugas at 10:54 AM on June 5, 2006

No.

If you're serious about wanting to reconnect with this person, call them and arrange a time when you can have coffee, a drink, whathaveyou. Whatever you have to say to them should be said in person. If you're unable/unwilling to do that... then let it go.
posted by papercake at 11:02 AM on June 5, 2006

reklaw - I pondered that too, and this is the trouble with anon questions that they can't clarify. I got the sense from the part of the question directly after where you end your quote that the poster doesn't feel that the insecurities have been resolved well enough to make a relationship workable, and that that would be expressed in the letter. I myself didn't get a clear "Now I do want a relationship with him" point to the question.

But, I could be wrong, hence the "this is what I got" opener and then also the second part of my advice. A letter is generally not the best forum for expressing these sorts of complicated emotions for all the reasons cited above. I originally had a bit about how hopefully someday the poster will be able to talk to him in person about the insecurities they used to have, rather than a letter about all the insecurities they did and continue to have, that they feel hinder a romantic relationship.

Hence, the point of my advice was that the poster needs to resolve/overcome these insecurities for their own well-being, then try to move forward and either rekindle a friendship or seek a romantic relationship.
posted by nelleish at 11:23 AM on June 5, 2006

Yes Yes Yes. Life is too short; have fun with it and lean from the pain.
posted by DrtyBlvd at 1:08 PM on June 5, 2006

Yes Yes Yes. Life is too short; have fun with it and learn from the pain.
posted by DrtyBlvd at 1:08 PM on June 5, 2006

ack
posted by DrtyBlvd at 1:08 PM on June 5, 2006

learn from the pain

which sometimes means you learn you shouldn't have done the things that cause pain in the first place...such as sending angsty emails.
posted by scody at 1:23 PM on June 5, 2006

I think part of the issue here is referring to the collected thoughts and clarifications you've written down as a LETTER. letters were meant to be sent.

If you think of it as a journal entry, maybe that will make it easier to figure out whether you want to share it with him, as the contents are probably there more for your benefit than for anyone elses.
posted by softlord at 2:27 PM on June 5, 2006

Post a somewhat ambiguous version to Craigslist's Missed Connections? Generally speaking, though, bad idea to hit that send button; do it in person if you really need to let him know. Oh, and don't hesitate on the therapy if you feel you're ready for it.
posted by redsnare at 3:04 PM on June 5, 2006

in the end, you'll only regret the things you didn't do.

ummmmm..... no.
posted by Afroblanco at 7:05 AM on June 6, 2006

Of course.
posted by Ironmouth at 2:25 PM on June 9, 2006