Ashley Dupre's Worst Advice Yet

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We know Ashley Dupre gives bad advice, but the over-the-top strategy she suggests for a man courting his coworker has really raised the bar.


Says an anonymous suitor,

I have a severe crush on a girl I work with. We've gone out a few times, but I'm pretty positive she has no clue how I feel. I want to express my feelings, but I'm concerned she won't feel the same way and if she does, might be leery of hooking up because we work together. What do I do?

You might think Dupre would advise caution, given that workplace romances can be touchy. You'd be wrong:

[Y]ou should try something creative to let her know how you feel. Since you're friendly and have gone out before, you're probably aware of some of her favorites: flowers, lunch spots, snacks, etc. I think you should send her things spread out over the course of a week. Sort of like a secret admirer. Start on Monday by leaving her an arrangement of her favorite flowers. In the card, write something like. "You know me and I know you, but I'd like to get to know you more." Let her be curious for a day, then on Wednesday, leave her a little something from her favorite lunch spot or a coffee place she goes to for a midday pick-me-up. With this one, get a little more personal in the card, and also give her some clues as to who you are. Finally, on Friday, leave a simple Post-It on her computer when she's not looking that says something like, "Have I driven you crazy enough? Let's meet so you finally know who I am (unless you've already figured it out!)" Tell her you'll be waiting on a certain day and time at a certain place with a single red rose. (I know this sounds cheesy, but I'm telling you, women go crazy for this stuff!)

If by "crazy" she means "scared that I'm being stalked at work," then she's right on. I find it hard to believe that many women would appreciate these coded messages at the office, especially given their vaguely creepy tone ("you know me and I know you"). Then there's the fact that the lady and her suitor have already gone out — isn't it possible that she's just not that into him? Leaving aside their previous history and possible sexual harassment concerns, though, is a grand gesture like this ever a good idea?

Sure, there are people who appreciate a well-thought-out Valentine, a birthday surprise, an elaborate proposal. But at least these are generally things that happen when you're already in a relationship. There's something about the overly complicated first-date (or in this case possibly second or third-date) ask that feels sort of pressuring — how can you say no, those flowers seem to demand, when I did all this work? And even if the suitor is a total sweetheart and never intended any pressure, all that extra planning makes a potential rejection way more awkward for everyone — plus he's out whatever money he spent at the florist. If you really must ask out your coworker, what's wrong with a basic, "wanna go out sometime?" It's simple, it's direct, and if she says no, at least no flowers had to die.


Ask Ashley: Love Work In Progress [NY Post]

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Let me tell y'all a story:

At my old college (I transferred) my nickname was "Kate Allinblack" cause uh, I wore black dresses everyday. Anyway, my boyfriend that I dated all of freshman year dumped me over the summer, and I came back for sophomore year a little bitter/leery.

There was this guy, whose name shall remain anonymous, who was *determined* to capture my heart. He set about this in several ways:

1. He wore all white every day

2. He gave me an orchid

3. For my birthday, he gave me a mini Zippo and a Colibri cigarette case (an expensive brand) with MY INITIALS ENGRAVED ON BOTH.

4. Wrote me letters in calligraphy. He learned calligraphy over the summer just to do this.

Was I flattered and swept off my feet? No. I was seriously uncomfortable. That was a couple of years ago, so now it's a funny story, but jesus, is it ever a step by step of what NOT to do to win a lady's affection.