Romantic or ridiculous: One New Yorker's citywide gesture of love

A local man has covered the city with more than 600 posters in an effort to win back his ex-girlfriend by Valentine's Day. Two TONY editors debate the pros and cons of this undertaking.

One of several posters an anonymous man has tacked up in various places around the city.

One of several posters an anonymous man has tacked up in various places around the city.

On my way home from a lunch date in Manhattan this weekend, the poster above caught my eye as I was waiting for the L train at Union Square. Naturally, as any journalist is wont to do, I snapped a picture, then hopped online once I got back to my apartment to see what more I could uncover about the mysterious viral campaign.

Evidently, the posters and their corresponding website, This Is How You Win Her Back, are part of one anonymous 30-year-old social-media pro's quest to re-woo his ex-girlfriend, who broke up with him ten months ago after what he calls "one of those arguments where neither one of us ever took the first calming step back." In November, he created the website and began hanging these posters all across the boroughs; so far he's up to 600 and has pledged to continue his efforts until Valentine's Day. "It is both an apology and a gesture to show her how much she actually means to me," he says via e-mail. "I wrote the Nabokov quote on a chalkboard in her kitchen when we broke up. She's a writer and a reader and a lover of books, and this is an homage to her just as much as it is to the city I love most."

While my initial response to the poster bonanza was one of warm fuzzies, other people have had a vastly different reaction. One of my Time Out New York cohorts, senior editor Amy Plitt, noted how off-putting she found the idea; when she posted about the site on Facebook, several friends also chimed in about their thoughts (most tended toward the ick, though some sided with aww). This morning, we debated the whole thing more thoroughly over IM.

Sarah: My initial reaction to TIHYWHB was definitely Awwwww!, with a dose of Hmmm, I want to know more. You seemed less than enthused by the campaign; what did you think after going through the Tumblr?

Amy: I had lots of thoughts! None of them were good! If a guy I had been seeing—and who messed up to a point that we broke up—suddenly took a private in-joke, or something like that, and plastered it all over the city, I'd feel thoroughly creeped out.

Sarah: I keep going back and forth. I'm a fan of grand romantic gestures, but I can totally see what you mean by it going overboard, especially in terms of the other person's privacy.

Amy: Yeah, exactly. There are grand romantic gestures and then there are things that creepy dudes do to try and get a woman's attention. Something like this, to me, is not so far off from those awful guys who get pissed off when they're trying to talk to a girl and she doesn't want to engage.

Sarah: Kind of like The Police's "Don't Stand So Close to Me" or "Every Breath You Take" should be playing in the background.

Amy: It's like when guys say, "But I'm so nice! Why don't you want to talk to me?," without considering that the woman has agency in this scenario and may not want to participate (or, in this case, may not want to get back together with the guy). It's totally an invasion of privacy. It just makes me recoil and feel really bad for whoever the girl is.

Sarah: A couple other people who commented on your Facebook post raised interesting points that have made me rethink this whole thing. For instance, the fact that it could be a grassroots marketing ploy for some yet-to-be-announced project.

Amy: I could absolutely see this being some kind of attempt to do viral marketing for a TV show/movie/Thought Catalog-esque website.

Sarah: In light of the whole Manti Te'o hoax, I'm even more skeptical. But the romantic in me is winning out so far.

Amy: Meanwhile the cynical, cranky feminist who is suspicious of most male motives in me is all like, Ewwww.

Sarah: Yeah. Though, your friend Mike had something interesting to say: "Now, I actually went to the website and I honestly think it's a perfectly acceptable tactic for the Millennial generation, who grew up with the understanding that every part of their lives is suitable for public display, and that the best way to get what they want is to 'go viral.' Want dad to buy you a dog? Put a plea on Facebook. Want a date to the prom? Hit YouTube." It's true that many people in younger generations have grown up with the mentality that everything can and should be shared.

Amy: It's a natural extension of all that, most likely. I doubt the guy behind it ever questioned that what he's doing could be seen as weird or as invading someone else's privacy. I doubt his intentions are bad, but considering that he admonished me about calling it out when you first posted the photo on Instagram (damn tracked tags!), I also doubt he's willing to examine how this could be problematic or misconstrued.

Sarah: Yeah, true. When someone is so deeply entrenched in his or her own motives and can't see the opposing viewpoint, that's when things can start to feel a little sociopathic.

Amy: Yeah, exactly. I wonder if he's considered how his ex would feel about this; someone on Facebook said that she must be the type of person who would go for grand gestures if he went through with this, but in my experience, a lot of guys just don't consider how their behavior will affect the women it's being directed toward.

Sarah: Or like when a guy proposes in public because he saw it in a movie, not because his intended likes that sort of thing. You have to consider your recipient/audience. Otherwise, you're making it about you, not them, which could be indicative of the behavior that got you in trouble in the first place.

Amy: Yep! And that's the other thing: If the dude really cared about getting his girlfriend back, maybe like, I don't know, find another way to show her that you're no longer a jerk? In addition to being over-the-top (and maybe fake!), this is a ridiculously huge ploy for attention.

Sarah: Fair point. It's hard to say without knowing her, but it's totally possible. Though, if she's not answering phone calls/e-mails/texts, any other gesture could feel equally stalkerish. Like showing up to her apartment or workplace with something or even sending flowers. It'll be interesting to see how it all pans out! 

Amy: Whatever the outcome, I'm sure I'll be annoyed by it!

What do you all think? Tweet Amy and me with your thoughts, and don't forget the hashtag #thisishowyouwinherback.

Follow Sarah Bruning on Twitter: @sarahbruning