Tuesday, April the 8th, 2008

I awoke last night in a cold sweat.

Actually, I awoke once many nights ago but I’ve just been too lazy to write about it. In fact, I wasn’t even in a cold sweat at the time—I just threw that in there for effect.

Like I was saying…

I awoke in a panic late last night, extremely conscious of my own singleness. After unsuccessfully racking my brain for the thoughts that concluded in my anxiety attack, I promptly shifted my focus to how I was going to remedy my situation.

And that’s when it started: I began cataloguing the list of people in my life I’ve genuinely been attracted to (at one point or another).

Now, I don’t have a really clear idea how that intellectual exercise helped me, but I’m now desperate to know from them the answer to the obvious question: “Are you married/betrothed/taken… or aren’t you?” And so, I’ve decided to take the bold step of just asking them. I intend on doing this via e-mail because that makes it all cold and impersonal, just ripe for this sort of occasion.

I think it’s going to read something like this:

Dear Admiree,

I’ve always had a bit of a crush on you, but never the guts to tell you so.

Hoping I’m not too late,

Of course, there are some shady aspects to this plan. In particular:

  1. I intend on sending this same letter to about three different women.
  2. In every instance, I’d be utterly devastated if I were to find out they’ve moved-on with their lives and want to have nothing to do with me. And this is where I believe my great plan falls apart.

In any event, I think the reason I’m bringing this up here is because I want to run it by you first. Just what would you do if something like this arrived at your doorstep?

This is a printer-friendly version of the journal entry “Dipping toes” from actuality.log. Visit to read the original entry and follow any responses to it.

22 Responses to “Dipping toes”

  1. Michelle says:

    It might not be that bad of a plan if you weren’t going to send the same email out to more than one girl. That’s kind of skeezy. :P

  2. V.R says:

    1. Better way would be to try finding out about them through any acquaintances/friends/contacts, if there are any.

    2. If I were you, and knew them then would’ve written in a more personalized manner.

    3. You should send the letter with an assumption that they most likely won’t respond – shoot blind-folded.

    4. If such a letter came to me from someone, oh well, (smile? blush? laugh?) and perhaps respond!

  3. anita says:

    first of all, i’d start out with a more general “what’s new with you?” kind of email, and depending on the replies you get to that, you can proceed with your original plan.

    are you planning on sending out all 3 at the same time? i think it might be better if you go in order of preference…unless of course, #2 and #3 might have some way to find out that they were not #1, should #1 reject you.

  4. pundit says:

    Michelle: You taught me a new word! (And since using new words in sentences is the best way to remember them,) It does sound a bit skeezy, doesn’t it? I just wish I had a better plan.

  5. pundit says:


    1. Are you sure? The thought of doing this crossed my mind earlier, but wouldn’t they think me nosy? More importantly, I am not OK with them giving me bad news and seeing me fall apart. (I supposedly have everything figured out.)

    2. I can definitely do that; I kinda like writing. (I think I deliberately tried to keep it terse… because I don’t want to let it show how much I care about their response.)

    3. Sigh. I want a reply—I want to hear there’s some hope left in this world.

    4. This is a response that’s piqued my curiosity. I must ask, your gender? (Should you choose to share it.)

  6. pundit says:

    anita: I (infrequently) keep in touch with these women, but expressly avoid the “What’s new with you?” spiel. I’ve been burnt by the the “Oh, I’m with this fabulous man now.” line too many times to count. I try to talk in (even more) superficial terms, trying not to provoke the surfacing of this very topic. Hmm… I think I now see my problem, and your point.

    I’m unsure of the probability of 1, 2 and 3 ever sharing a table at a coffee shop comparing letter similarities (and timestamps!) but the remote possibility does exist. Either way, I just realised I’m too much of a chicken to pull this off (in any form), and I’m going to let them all go (later, if not already) just for fear of hearing the wrong thing.

    I am entirely hopeless.

  7. anita says:

    Isn’t it better to hear “Oh, I’m with this fabulous man now” than “I’m flattered, but I only like you as a friend.” I mean, it can save you a little embarrassment (if you are the type to get humiliated when something like that happens). But, being entirely hopeless myself, I kinda understand…

  8. anonymiss says:

    While there is the charm of honesty and boldness in this mail, there is a thin line between this genuine communication and the 101 ‘will you do friendship with me’ type mails.

  9. pundit says:

    anita: Are you sure? I think I’d rather hear the latter rather than the former. I interpret it as leaving more wiggle-room. (Even though it doesn’t.)

  10. pundit says:

    anonymiss: What if I’ve known these women since I was 10–12? Would it still be construed as a 101 ‘friend me’ e-mail?

  11. anita says:

    Well, to me personally, the latter would feel like rejection, and I don’t like feeling rejected. But if you’re ok with that type of response – and with the possibility that the girl might avoid you forever – then go ahead.

    From my perspective, once when a male friend suddenly told me that he was interested in dating me, it made me want to run the other way. I wasn’t scared – just grossed out by the idea because I wasn’t attracted to him and had never thought of him as anything more than a friend. I only saw him once after that, and it was akward as hell. Haven’t heard from him since. Anyway…my point is, if he had been more subtle about it, I would have probably gotten the point across without having to make things all weird…

  12. pundit says:

    No, I am not OK with being avoided forever. And I am even more not-OK with things being all weird forevermore.

    Which means I’m screwed. Because now—realising how much things can go awry as a result—I am definitely not going to try. Allowing some random dude to waltz in and walk off with her.

  13. anita says:

    I didn’t say not to try – you should definitely try. I just think you should take a more subtle approach.

  14. V.R says:

    4. Lets say I belong to “F” community – From what you’ve said, having known each of them for considerable period of time, perhaps you would know the kind of person each of them are. They, having known you for so long, all the three – Smile, Blush or Laugh are possible, also the remote possibility of outright rejection.. And, since you are not writing-talking to a stranger, chances are even less. Pick the most suitable way as you think for each. But, I agree with anita, subtlety is the key.

    Lets say I belong to “M” community – I would rather take the risk, preparing myself for the worst. At the most having such a conversation in a playful manner without being overboard. Oh yes, if someone would have said the same to me – I would still smile, blush or laugh.

  15. Fellow Retard says:

    I would prescribe a dutiful dose of Robert Greene’s Art of Seduction.

    The mere fact that you are trying would make you seem of little value to the women who are higher than you on the attractiveness scale.

  16. J says:

    What would I do if something like this arrived at my doorstep? Well, it didn’t.


  17. Luke H says:

    I’m seconding Fellow Retard. This is a desperate measure.

    Now I understand where you’re coming from; I used to be there. But I’m telling you, there’s another way.

    Before you embarrass yourself, why not educate yourself on how to attract women? There are many online resources, one which helped me out was Double Your Dating with David DeAngelo.

    What have you got to lose … apart from that wobbly feeling in your stomach whenever you think about approaching a woman you’re interested in!

  18. pundit says:

    anita and V.R: Hmm… it’s been a while and I really haven’t followed through with (any variation of) the plan. This isn’t really surprising as, like I said earlier, I’m just a big chicken.

    But I am curious, why is subtlety so much better? If I were to go with a more subtle/playful version, what really changes? As in, once the question is posed (in whatever words), and I receive a negative response (in whatever words), aren’t things going to be awkward (and generally screwed) anyway?

  19. pundit says:

    Fellow Retard and Luke H: As much as I expect it, it’s always fascinating to me how conflicting opinions presented here often carve up along gender lines.

    I understand what you two are driving at, but what’s wrong with desperate measures for desperate times? (Unless of course the obvious: They just don’t work.)

    I’m not aiming for anything major, just trying to start a conversation with my cards on the table. Oh, and not screw anything up.

  20. pundit says:

    J: I’ve figured out how to lose without even playing.

  21. anita says:

    I suggested being subtle in order to not make things awkward. When you’re subtle, a girl might start to suspect that you might be into her, but it’s still possible that you’re not and you’re just being friendly. There’s a huge difference when someone directly informs you that they’re interested. So if you’d like to avoid awkwardness and potentially screwing up your friendship, then I think being subtle is the way to go.

    Also, in response to some of the other comments, I think there’s a difference between meeting/attracting/dating women in general and wanting to date someone that you’re already friends with.

  22. V.R says:

    Couldn’t agree more!

8,938,055 people conned into wasting their bandwidth.