An Open Letter To Women I Am Interested In

Ladies, and I say that because Demetri Martin has proven that if you end any sentence with that it becomes creepy but had nothing to share about starting with it,

How are you doing? Just trying to keep things casual and upbeat [and polite, because I am Canadian, after all] before we move on to a subject I’m trying to form an opinion on. You can be sure that if I was even 23% sure of myself this would be a post that confidently projected my opinions as being truths, but alas, here we are.

Last week I came across an article on the AV Club on what you probably know to be one of my favourite shows: Brooklyn Nine-Nine. It concerned one character in particular, Detective Charles Boyle, and how much of the season followed his attempts at wooing fellow officer Rosa Diaz. Now they weren’t, and I’m not, making any comments about workplace romances- the focus was instead on the fact that she was clearly not interested in him.

That’s just a single exchange from a short montage that includes three, the last of which has her holding his face in one hand and telling him “Listen to me! The healthy thing for you to do is move on.” His behaviour does not stop there, however.

The article, which bears the subtitle “The day of the Nice Guy is over”, goes on to say that playing this sort of thing off as comedy is inherently problematic because:

“A generation of romantic comedies rewarding men for diligently pursuing a woman until she caves has normalized a behavior that has direct and unwelcome corollaries in real life. “

It’s all fun and games until it borders on actual harassment. I mean, arguably it stops being fun and games before that, because it must be frustrating to tell someone “no” only to have them persist.

Here’s the thing for me personally, which is that it’s not even just TV shows and movies that has caused this idea to stick with me [though they’ve done the majority of the heavy lifting]. When I was in high school one of my best friends told me that his brother-in-law asked his sister to marry him three times before she said yes. I never asked for him to specify any sort of context, but I can remember being in awe of the guy. “Yes,” I thought, “Hard work pays off.”

With those four words in mind women of potential interest become either dikes [no puns here, just keep reading] or foxes. In the first scenario all of the unrelenting attention eventually serves to erode and break down the barrier, flooding the farmlands, villages, etc. with the seawater of your love. In the latter she’s just “hard to get”, and after putting in enough effort you’re sure to catch her because, after all, she’s just playing games. Release the hounds, etc.

I guess what I’m asking here, la- women I would like to maybe date one day, what do I do? To be completely honest I am terrified of being just another guy out there bothering women. I realize how difficult even being female and on a dating site can be, and the last thing I want is to make people feel uncomfortable or, heaven forbid, unsafe. If I send a message and don’t get a reply should I try again, is the first one left unanswered a resounding “No”?

Perseverance and tenacity are both words that I’ve heard upheld by both sexes. “Be confident, if you give up too easily it’ll make it seem like you don’t care.” I don’t think I have any danger of turning into an actual full-fledged Charles Boyle [or the wounded friend zone detainee], I just want more solid guidelines. It’s not going to take someone telling me to my face to move on to send the message, but what about less extreme cases?

The AV Club’s review of Brooklyn Nine-Nine‘s 13th episode applauds Boyle’s parting lines to Diaz as he explains why he took a bullet for her:

“I did what every good cop would do. And when you finally go out with me, and you will, it’ll be because of things only Charles Boyle would do.”

I chalk it up to the sincere tone of Lo Truglio’s delivery that made it so that viewers didn’t immediately balk at his character straight-up telling another that she would inevitably date him. Personally, I’d rather say the right thing instead of saying it right way.

So, women who are reading this both on the market and off, what advice do you have for me? Is the line between “cute” and “creepy” really that narrow, or is it better to be safe than sorry [about making people feel uncomfortable]?

Anyway, thanks for reading this message meant for a few hundred million people all over the planet. Don’t all respond at once, but it’d be rad if some of you did.




10 responses to “An Open Letter To Women I Am Interested In

  1. If this is inadvertently about anyone specifically, just go for it! I’m sure ladies appreciate boldness.

  2. Fortunately or unfortunately (depending on how you look at it) most of what happens when a girl is deciding if a guy is being cute or creepy comes down to how she already feels about said guy. If she thinks he seems like a funny, interesting, attractive person, what he says will come across as cute and flattering. If she already thinks he’s creepy, he’ll come across as just being his creepy self. So basically, if you say something that’s borderline creepy and a girl responds positively, she’s probably interested in you.

  3. I think most women find it nice when a guy shows interest, but too much persistence can result in feeling awkward telling a guy no if a girl is not interested, or if she caves and goes out with you it may not end well if her heart was not in it to begin with. I’ll be honest, I have been the girl who caved and dated the guy I was not initially interested in and it did not end well. I also had to tell a guy very awkwardly that I was not interested in him after he was so persistent that we hang out after I said no, and apparently he thought it was a date but I did not (awkward story). Anyways, balance is important and each scenario and girl will be different. If you never put yourself out there you may never know. Girls send a lot of hints so try and get a feel for each situation. I also agree with Beth’s point.

  4. So I feel like what is key is the difference between being direct and bring creepy, and the assumptions about the other party involved in each of those. Being direct would involve being assertive but accepting of the other party’s directness and autonomy. Being creepy doesn’t allow the other party to define themselves, and assumes that the woman in question is either a) unaware of or b) lying about her real feelings. The first is usually misogynist and presumptuous, and the second is either masochistic or unwise. Id say the ideal proposal would be direct but appreciative of the friendship. If you like someone and want to spend more time with them, you should tell them that. If you want to be romantically involved, I think the ideal way to approach that would be to make your intentions clear, and also make it clear that you’d want to continue being friends of the intentions aren’t reciprocated (if that’s true – and it usually should be), and then (this is key) asking him/her what his/her intentions are, and them believing the answer. I think that’s the most important thing that’s lacking in creepy approaches: the acceptance of the other party’s autonomy. And earnestness. False confidence, general douchebaggery, smirking, presumptuousness: all will attract the type of person that I wouldn’t recommend for a longish term relationship. Assuming that that’s what we’re aiming for.

    Soooo, in a nutshell (I’m terrible at being succinct on my phone), a) be earnest and direct and b) allow & expect the other party to be direct. Oh, and c) appreciate a friendship with someone you’re crushing on for the time that you get to spend with that person, about whom you ostensibly care.

  5. I’m just reminded of the Dobler-Dahmer Effect from HIMYM, don’t know if you’re familiar with it or not.

    And honestly, dang. What a tough thought. I really feel like it all depends, that there isn’t a standard. Everyone is just different with their own experiences and expectations. Some women will be a firm no, some like the chase. I guess you’ll never really be sure until you try.
    From your end, do you want to “win” someone over? It is a valiant idea that you were able to succeed, or does it tell you that it was too much effort, maybe it’s not entirely genuine?

    People are too complicated.

    • I appreciate any and all references to How I Met Your Mother. The Dobler-Dahmer Theory, for anyone who may be interested, is in essence:

      “If both people are into each other, then a big romantic gesture works: Dobler, but if one person isn’t into the other, the same gesture comes off serial-killer crazy: Dahmer.”

      People are too complicated.

  6. Knowing your gal is important. If she’s the playful type, she may respond well to as many as four well-spaced-out attempts, but never more than that. If she’s like me and hates feeling like she’s being told what to do, never more than two attempts or you risk making her feel bullied or commanded. As for the, “You *will* come around eventually” line, never use it. I myself have felt and still do feel this way about a guy, so I know the feeling. But I would never say it, because it is no one’s job to tell someone else what their future should be, much less what their future *will* be. Unfortunately, the line between “cute” and “creepy” really is that fine. : p One of things that simply can’t be made any easier to figure out, I suppose. Oh bother.

  7. I feel like there’s a couple possible outcomes when someone asks someone else out (for the sake of this discussion, dude asks lady out):
    1.) She’s into you and says yes
    2.) She’s not into you and says no
    –>In this case, I wouldn’t say that going after her until she finally gives in is the best way to approach this. I mean, it might eventually work, but you’d really be better off using the time and energy into making yourself a more awesome person, rather than obsessing about her. If she’s into your awesome, she’ll come around on her own. If she’s not, then she obviously has terrible taste (despite being an otherwise wonderful person, I’m sure), and you cannot fix that. Stop trying. There are other lovely ladies in the sea.
    3.) She’s into you and says no
    –>In this case, she probably has issues not related to you that would make her not-currently-awesome relationship material. Maybe she comes from the school of thought that says you need to establish dominance over your prey/man early in the relationship. Maybe she is currently incapable of honestly communicating her feelings. Maybe she’s very self-aware and realizes that she’s just not ready for a relationship at this point. There are a plethora of potential problems, and (despite the position you may or may not hold in the center of the universe) you are the solution for zero of them. Let her get her shit together in peace.

    Summary of my thoughts: If she says no, there’s probably a good reason for it, and even if you could “wear her down”, you probably don’t want to.

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