Welcome back to "Ask Jess, Dammit!"
Gathering from the amount of emails I found in the Maxim mailbox (maximaskjessica@gmail.com), I think it's pretty safe to assume that the first installment was a roaring success! Glad you guys enjoyed it and found what I had to say both amusing and helpful.

Now that the bar has been set, I'll make sure that each article remains steadily below it!

Enjoy!

Why the fuck do they talk about themselves all the time?

I might be able to change the subject completely, but most girls always end up in some way or another talking about themselves again. It's ûber-annoying. Seems as though they want sympathy for something, considering most of the time the subject ends in her saying something like: "...and i twisted my ankle that very night!". From there the subject might change to work. Then she'll start bitching about how much she's been working lately.

The reason why this can be frustrating is because it forces the guy to just sit there and nod his head, considering how the girl is talking like the entire conversation is one single story. Like she's reading to you from a book (okay not that bad but almost).

A lot of my friends agree on this, and the fact that you don't have to be on a date for this to happen of course. It can simply happen in any friendly conversation. I'd say that 6 out of 10 times you have a longer conversation with a girl, this happens.

Why do you think this is, and thinking back: Do you consider yourself to be one of these girls?

JESS: I do consider myself one of these girls. I am also very aware when I'm yammering on and yet, I can't seem to stop myself. I think the same goes for the women you are referencing. While I see how it can be annoying to you, I think you should also consider changing your perspective and looking at it from a different point of view.

See, often when I keep blabbering on about myself it's because I'm trying to identify or add to the conversation rather than searching for any type of sympathy. So, if you're sitting there telling me how hard your work day had been, I want to pipe in with how hard mine was so that I can show you I empathize with your problem and thus, a connection between the two of us has been established.

It reminds me of this one time when I was hanging out with this guy and he was telling me all about his various international travel excursions which, obviously, prompted me to tell him about how I had been to several other countries and how much I enjoy traveling even though it was starting to get old because I travel way  too often nowadays. Especially since IGN has me flying back and forth between Brisbane and LA every week to film our shows. Brisbane is our main headquarters so that's why I have to keep going back. They built our video studio there which, between you and me, was kinda' stupid. I remember this one time trying to have a lunch meeting with my boss about how dumb I thought it was for the video team to be building a studio in San Francisco when everyone and their mom knows that LA is where you go to film stuff. It was a great discussion so that was one small victory. Unfortunately, the victory ended there because I up and twisted my ankle that very night! DOH! *giggle*

FORGET A GRAND SLAM. JUST GET an at-bat... 
Q: Hey Jessica,

I'm in Sixth Form (That's college I guess, for those of an American/Canadian disposition) and I'm still yet to have a girlfriend. Heck, I've never really been on a date. I know dating/girlfriends aren't necessary at this point in life but I still feel like I'm missing out and such. I'm not just looking to get laid.

Basically, out of the last 6 or so attempts of asking girls out I've been shot down each time. I just don't get it. I've took every other approach under the sun and still nothing...I don't get it. In person, I'm funny, nice, sweet, kinda smart and such...yet still there seems to be no interest.

Am I going for it all wrong? What can I do to help improve my chances/succeed for once?

Also I can't seem to be able to talk about things other than movies or video games...Any chance of helping on the thinking of topics front?...

Thanks for reading, understanding and (hopefully) answering.

—Your huge British fan, Chris.

JESS: While I understand your conundrum, there are a few details that are lacking in order for me to give you a really solid response. Mainly: What type(s) of girls are you going after? I'm not asking this because of the whole "are you shooting for someone over your level" thing or anything like that. I'm legitimately curious because I am a firm believer that having things in common really makes a difference when trying to land a date (and, having then landed the date, making it a successful one).

The allure of a beautiful person is strong, but it all falls apart if you find that there's nothing to talk about. That being said, you've waited a decent amount of time before jumping into the dating pool. Why not just extend that same patience a little longer and scope out an individual you know you would have a good time with? There's absolutely NOTHING wrong with wanting to talk movies and video games and with the ever-growing demographic known as the "Girl Gamer," you should be able to find a cute little nerd of the female variety to share your hobbies with.

Also note: Oftentimes women get a bit nervous when random men that they have no association with ask them out. Rather, they prefer to date guys they already have some type of rapport with (thus all the couples who were "friends" before they started getting it on). I know it sounds kind of stupid. After all, the whole point of dating is to get to know someone. But in today's society, one cannot blame women for being a bit skittish towards strangers. After all, you might look and act like the most normal and nice guy in the world, but so did Ted Bundy.

Just keep that in mind next time you go up to someone and ask them out. If you don't have some sort of common thread between the two of you—i.e. are in the same class, know some of the same people, etc.—then you might find yourself rejected more often than not.

I'D  YOU, BUT...MY JOYSTICK IS BROKEN?
Q: Dear Angelface,

My GF has recently revealed that she would like to spice things up in bed; I was at first hoping she wanted to include her sister, but sadly she has other plans. After we had a "talk" she said she would like "it" "rougher", which is kinda f'd up to a delicate flower such as myself, don't get me wrong or anything, I would hit a woman to defend myself, but what the hell exactly does she expect? A Shoryuken. A Tiger Uppercut in bed? When I asked her, she said to just go with the flow and let it come naturally...NATURALLY...Last time I hit a girl was in eighth grade when my sister gave my cousin my O-Town CD. Anyway how do I break up with her? She's obviously mentally unstable...right? —Doug G

JESS: First of all, don't ever call me Angelface again. Even if it is true.

Secondly, I think you're being an idiot. You have a g-friend that says she wants things to get spicier and you want to dump her!? Granted, your attempt at humour by referencing Street Fighter maneuvers to cover up the personal shame at knowing things might be falling a bit short in the sack did, for one quick second, appeal to my nerdy side and almost...almost...made me feel sorry for you.

Here's my advice: grow a sack, go to a sex shop and pick up hand cuffs, a ball gag, some dildos and a video on "How To Please A Woman."

WAIT—GIRLS PLAY VIDEO GAMES, TOO?
Q: Dear Jess,

I've been wanting to buy World of Warcraft for some time now but have been reluctant to buy it because of the reputation that surrounds it. Anytime I've mentioned WoW to my friends I always get a response like, "Only nerds play that" or "You're never going to get laid ever if you play that." What's the best way to respond to this? —Steve

PS. I would like to play WoW and still get laid.

JESS: Steve,

WoW is a phenomenon. EVERYONE (Editor's Note: Almost everyone. Ehem.) plays it. Which means that everyone could/would lay you. Potentially in character.

Seriously though, just start sending your frenemies links to pictures of Frag Dolls, Morgan Webb, Olivia Munn, maybe even that chick who hosts IGN's stuff and all of the rest of the gamers out there who sport a set of tits. That alone should get them to shut their WoW-hating stupid poop mouths!

ALAS, A NEW WORD IS BORN: MEGA-BAGGAGE
Q: Jess,

Great to see you on Maxim! As a trusted voice to 21st century males everywhere, how do I get on track with this...

I have taken up the cause of career growth over the need to "have" a woman, now that I'm at a place of success, willing to open myself up to a relationship, I'm quickly discovering that I left my "game" in the context of my younger 20s. Flirting is cheesy... you see where I'm going.

How do I shed that mantle to meet those 25–29s who either still haven't found love, or are recently unshackled? —Andrew, Tampa, FL

JESS: Hey Andrew!

Let me just start this off by saying that I meet more and more people in this very same conundrum every day. (I also include myself in with this mix.) I have had tons of late-night, semi-drunken, soul-baring discussions about the enigma that is the mid-20s to mid-30s dating scene. I could go into sociological and cultural rundowns but I shall spare you that and instead, simply state, that it's a f*^&ing disaster.

I honestly believe that it is the most difficult dating demographic to be in. Nine times out of 10, you will run into someone who is either already married, recently divorced (and thus temporarily bonkers), divorced and normalized, but comes with MEGA-BAGGAGE (aka: kids), or is none of the above and can therefore be deemed as socially inept and/or insane.

This means you have a snowball's chance in Hell to accidentally run into someone who is in the same boat as you (career focused and thus missed out on the hook-up tip). If you do, through some weird twist of fate, come across an individual of like caliber: snatch them up, love them with all of your heart and be forever and eternally grateful.
 
Or, you can bite the bullet, hook up with divorcee with kids and just accept and love being a part of an instant family. There's nothing wrong with that-it's just a matter of taste.

One thing I recommend you don't do (and is the most common mistake I see men make), is to start dating a much younger girl. While I am fully aware that the fresh flesh of youth is alluring (you're talking to a woman whose last few boyfriends have been much younger), if you're looking for something serious, and it sounds like you are, oftentimes age differences will cause that to fall a bit short. (Again, I'm speaking from experience.) Don't use the easy accessibility of youth as an excuse to get rid of your loneliness. Hold out for a better and brighter thing. Your heart, mind, and wallet will thank you.

PS: Last thing: Don't look for love in bars. I'm not saying you won't find someone amazing there, but the chances for a real relationship blossoming from such an encounter are pretty slim. If you walk into a place and see a mechanical bull, a bunch of pink-hued martinis, and the same type of halter top in different colors: take a deep breath, turn around and walk your ass back out of that door.