All I Want for Christmas Is You (in Bed)

Santa didn't answer my wish, you weren't under the Xmas tree this morning.
- Male, 32

Dare I ask whether you wished me to be wrapped up just for your opening pleasure? I really would have felt better if you had given me more details about your wish, because when I first read your message, this is the only thing that came to mind:

Closet Lesbian? LesbiHONest

This one came from a random OkC girl, and it was sent to a fellow OkC girl. It's quite unfortunate that when it comes to sending online dating messages, the girls can be every bit as tactless as the guys.

hi - you are very sexy! 
would you be interested in doing a 3sum with me and my boyfriend [name redacted]? 
please let me know 
thanks,
[name redacted]

From a utilitarian standpoint, this girl hit the mark perfectly. She opened with flattery, conveyed her main point in just 10 words, politely solicited a response, and closed with her name. And we are on the INTERNET, after all, so chances are that if she copypastas this message enough times, she will eventually get an affirmative response. But alas, from the standpoint of normal, functioning, non-sex-addicted individuals, specifically the straight females she's sending this message to, this sort of inquiry will get her nowhere but smack dab on the front page of MessageMeNot. Dear skeevy girl: you fail. And "3sum" sounds like a calculator game. 

Sugar Daddy Needs Audacity of Hope

Hello - Please don't be offended by message. It Is not to meant to cast aspersions on anyone or make any judgements about anyone. For a long time I have thought it would be nice to have a discreet friendship with a younger lady. I am widowed and currently not seeing anyone.I do not like one night stands and yet don't want to be married again at this point. I would like to meet someone nice for an ongoing friendship. If this situation seems at all appealing to you then please check out my profile and get back to me. I will make a great friend.
- Male, 59

Correct me if I'm wrong, but doesn't "discreet friendship" by definition imply sex? I feel like this guy should just market himself as a sugar daddy. But then again, maybe the reason he's on a free dating site is that he has no sugar to give :(.

Also, seriously? He's 59 years old and soliciting sex from a 21-year-old? This guy is as ballsy as he is euphemistic -- and depressing. Note how his terminology steadily grows more and more hopeless, ranging from "discreet friendship" to "ongoing friendship" to simply "great friend." Maybe his aspirations are getting lower with every sentence he types. Methinks they were a bit too high to begin with.

Don't Stop Believing (In Boobs)

It's seeing the hope within a person like you that gives me so much fuel to carry on fighting for today and tomorrow in the name of Humanity. I deeply thank you for you being here.
- Male, 21

Come again? Do you, like, have a terminal illness or something? And what exactly was it about me that inspired you so much? Was it the part of my profile where I quoted that Journey song? Or maybe that I mentioned volunteering at an animal shelter? No, wait! Was it the cleavage pic? It MUST have been the cleavage pic. Cleavage gives you the strength to carry on, right? Gah, so many unanswered questions!

40-year-old Man Likes Little Girls with Big... Brains

...and he cannot lie, you other pedos can't deny:

tell me, how did they get your brain into that 19yo little girls cranium..!?
- Male, 41

According to Miss Manners, "little girl" is acceptable to use in ONLY two circumstances: (1) If you're trying to help me lie my way into a student discount, or (2) If we're doing one of those kinky "daddy-girl" role play scenarios. Given that your first ever message to me occurs in neither of these circumstances, perhaps you should take some sound advice from the Moral Lizard:

Love at First Slight

Consider yourself stomped harder, you closet man-hating leftist, pseudo-intellectual, heterophobic douche. not even one star. 

- Male, 35

Something tells me this guy could use some advice on crafting pick-up lines. Needless to say, our friend didn't take this guy's message very lightly. Here's her reply:

I'm really pleased you used the relatively gender-neutral insult "douche" (which while we often use it to define dudes such as yourself, refers to vaginal washing. For the record, I would never wash my vagina with you.).

I generally prefer to use the term "asshole," as in "You Are a Fucking Asshole." Because while not everyone can be a dick or a cunt, everyone, including you, has and can be an Asshole.

Does the fact that she replied mean that she's interested? Probably not, but I'm sure he'll interpret it that way...

Those Who Make Passes About Glasses Lack Foresight

If you take it out your glasses ,.you looks sexy but when you take the glasses , you looks ugly :)

- Male, 24

This guy is quite the Casanova. And he's quite strategic in his sentence structure. He sounds juuuust illiterate enough for me to not know for sure whether "take it out your glasses" means a) take them out of their case for the purpose of putting them on, or b) take them out (off) my head. Granted, it remains perfectly clear that in one of these cases, he thinks I'm totes fugly. He kind of makes of wish I didn't wear glasses, because having to look at his sorry ass with four eyes is twice as depressing.