ASSk Joanna: Saying “I Love You”, Getting Her To Say Yes To Anal and Rim Jobs!

Dear Joanna,

As a
27-year-old, straight man, para-professional from the NYC metro area,
in all my years I have yet to say those powerful three words: "I love
you". While plenty of beautiful girls and women have made their way
into my life more often than not, I'm stuck in the friend zone before I
can develop a closer relationship. When not delegated as friend, I'm
left for the bigger, better deal which is usually a guy with more
money, more muscles, or a Mercedes. At 6 ft, 200 lbs, with light
features, strong arms and a college education, how can a shorter Vince
Vaughn look-a-like attract his first love? Is it too late, has time run
out? How do you suggest I look a girl square in the eye and mean what
I've been longing to say all my life? (I <3 you)- Hopeless Romantic & Burning Angel Fan

If
it makes you feel any better, I don't like guys with muscles...and
someone who is dating someone because of the car they drive or how much
money they have is not worth dating anyways. Time has not run out!
Unless you are like, 97-years-old. If you are over the age of 90, then
yes - I am sorry...I think your time has run out.

OK, well if
you are not over 90-years-old, then here is some advice. I think you
might be trying a little too hard...and it might be a little
unattractive. Girls are not attracted to guys that aren't
confident...well, I take that back. You either need to be really
confident, or like, suicidal. Some girls really like confident
guys...and some girls like guys who are really emo and depressed and
want to kill themselves. I don't know why; I never really did. No wait,
I am lying...I totally did. But that was a long time ago. So maybe you
need to decide what direction you want to go in - either be a super
confident man and be like, "Yo, I am awesome...if you wanna date me,
cool, if not...well, whatever, it's your loss." OR you need to go in
the other direction, and wear lots of black, and carry around some sad
books, and listen to Bauhaus and want to die. Being somewhere in
between those two places is just gonna get you nowhere.

But
this is all advice on what to do IRL (that is dork-speak for "in real
life"). If you are picking up girls on the Internet, you have some more
leeway. If you really want a serious relationship and you are worried
about being rejected, then I would say sign up for any of those
match-making websites. Like Match.com, or OK Cupid, or Adult Friend
Finder - I mean, sign up for all of them and see which one works. But
just be yourself, or maybe figure out who yourself is first. If you are
gonna be talking to a lot of girls, you need to have things to talk
about. When you sit down for a dinner date and a girl says "So what do
you do?", you don't want to say, "I sit around all day hoping that I
will find someone who will fall in love with me..." because that would
be really lame.

Dear Joanna's Bottom,

How do I convince my girlfriend to do anal?

Sincerely,

A-Hole Lover

Why
do I feel like I get asked this question every week? Ladies, can you
all start giving up your buttholes to your boyfriends because I am sick
of telling them how to get you to do it. I feel like it's all anyone
wants to talk to me about.

I don't know your girlfriend, or
anything about her, or her body, or anything she likes, but I think the
best way to ask for anal sex is in the heat of the moment. Like one
night, when you're having really good sex, just be like "Baby, I wanna
put it in your ass"...but it needs to be REALLY hot sex. She needs to
be having crazy orgasms. You guys need to feel like you are on a
different planet - like that type of sex. When you're a chick and you
get in that mode, you will agree to almost anything. If you don't have
that kind of sex in the first place with your girlfriend, then anal sex
probably won't happen.

Hi Joanna's Butt!

Who gives the best rim-job - guys or girls?

Do u prefer a tongue or a cock up da butt? Thanks!

Yours Truly,

Crack Head

Um.
Well, some girls give terrible rim-jobs and some girls give awesome
rim-jobs and some guys give awesome rim-jobs and some guys give
terrible rim-jobs. I would have to say the two best rim-jobs I have
ever gotten were from 1) Belladonna and 2) Steve Holmes. They just both
happen to be really experienced with this stuff. Steve really loves it
when chicks eat his ass so he just kinda knows what to do. And I think
Belladonna invented asses in general. I don't think anyone had them
before she came around, so she just knows what to do.

I would definitely prefer a cock over a tongue in me.