I would say not to bother with the feminine wiles. I can understand Becky’s point, and I’m not above batting my eyelashes for a good cause (i.e. when surveying radical Republicans at a town hall meeting in an attempt to understand why they believe what they do. I find people are more willing to tell you things like that if you let them take you for a dumb girl, galling as that may be, since they will see an opportunity to ‘teach’ you why they are right. Not that I really came out much the wiser in that case, since it was pretty much all hyperbolic nonsense.)

But here, you have a legal right to compensation, you’re not asking him for any extraordinary favors. And even if he wants to ‘shut down’, he has no choice but to face up to you and the shitstorm he created.

I’m falling asleep in my chair, so I hope that made sense!

I don’t know where you live, but if it’s in Illinois, the relevant law is Section 715/2: http://www.renters-rights.com/html/illinois.html. I assume other states also have the text of the laws on-line somewhere, and some city ordinances are more generous to tenants than the state laws. Citing a particular legal code makes threatening a lawsuit more credible.

Then, if you actually need a lawyer, a lot will make contingency arrangements. (They don’t get paid until you do, and then they just get a percentage of that.) Try http://www.naca.net.

That being said, if dragging this creep to court was going to be a nightmare, I would be inclined to follow Psyche’s suggestion. It would, in my book, at least be worth a try to play to his ego and attempt to extract the money (relatively) painlessly.

Either way, you have my utmost sympathies.

But in general, I don’t think it’s necessarily unethical to use cultural stereotypes to your advantage, in certain situations. I rarely do it specifically via my femininity, but do tend to lean on my relative youth, and the fact that I look like a very nice, Polish, young lady. So rather than be all “I’m a sexy lady fall for my sultry ways and do my bidding,” it’s more “Oh come on man I could be your daughter! What would you want someone to do for your daughter if she were in this position?!” It’s not the best thing for the movement, but there are some things that are really non-negotiable for me, and for which I kind of have no choice but to do what I have to do to get what I need (like things having to do with money, because I’m poor). Also, I don’t usually do it consciously. Like, when I got a speeding ticket in college and was going to have to pay $300, but the judge asked me what my father did when he found out that I got pulled over (the car was in my dad’s name), I was like “Oh, he yelled at me,” implication: like you would have if you were my dad. I didn’t have to pay. I didn’t really realize I was doing it at the time, though–the judge just kind of looked like my dad, so I responded accordingly. Though, I actually never speed now because I’m so scared I’ll get pulled over again, so the laws: they work!

When I do choose to do it, it’s usually because the person I’m dealing with is an asshole. If it’s with an annoying person–like, say, someone who owes me something and appears unwilling to do it, I might start playing roles. But once it becomes clear that they will not give me what I want, or once they do give me what I want, I revert to mean old me. Like, “Good thing you gave me my security deposit–it would have been so annoying to take you to small claims court! Ha ha ha.”

Playing to type isn’t good. But also, if there’s a person who is so dense that they will encourage, or expect, you to play that part in an interaction, they are the type of person who will hold on to stereotypes no matter what you do. So, if you’re assertive and firm instead of giggle and cute, you’re just a bitchy bitch bitchy. If you giggle, you’re a woman with wiles who manipulates men. Some people just will. not. change, and if you have to deal with them, sometimes it’s just best to recognize it and do what’s easiest.

I think the people giving you the advice to be the one to work the landlord have misguided (and in this case) overly optimistic ideas about the myth of young women’s “power” in this society. If merely batting your eyes and being young and cute was enough, those interns wouldn’t have been screwing David Letterman, right? Feminine wiles isn’t going to work. In my experience, using the much touted “power of female sexuality” doesn’t actually gain a girl or woman much – unless there’s something exchanged beyond flirting and eye-batting. Not to say “don’t flatter yourself”, but don’t flatter yourself – the neighborhood is filled with pretty young hipster women, and just being ingratiating eyecandy isn’t enough to get someone to roll over and give you money.

I say don’t compromise your values on this one – partly because it’s not gonna work anyway. And I call bullshit on the people suggesting that the landlord will react better to you asking for the money – sure, he might be more polite if you act flirtatious and accommodating and nonthreatening, and happier to see a young woman than deal with a man, but it doesn’t mean he’s gonna pay up. I think the people suggesting this course of action see young women getting attention from men, but don’t understand that this attention rarely translates into free goods and services – you may get a door opened for you, the guy at the bodega may flirt with you, and the landlord might smile and drool over you, but when was the last time a business owner gave you free stuff just because you’re pretty?

Getting money from a NYC landlord is rough. I live in the city too – the laws are not as tenant-friendly as one would hope. Good luck.

We had a similar situation that– after several polite phone calls asking for return of a deposit– I handled w/ a nice, scary letter with “Esq.” at the bottom. (Convenient perk of being an attorney, likely unnecessary.)

Basically I learned my rights for small claims court. I told him he could return my deposit within 2 weeks of the letter or I’d begin small claims court. I found out I’d be entitled to my deposit, plus three times my costs (including the cost of returning to another state to fight it.) I estimated the total cost, and plain old cost-benefit analysis showed him paying up would be cheaper.

I always appeal to raw economics.

But really, I think it’s best to skip straight to the pleasant but knowledgeable letter. It’s likely he’ll pay up rather than risk a court case and having to pay far more later. Good luck.