Ask Jess, Dammit! Vol. 5: Learning to Grow Some Man-meat

Welcome back to "Ask Jess, Dammit!"
Hey all!

Just about to head off to Monte Carlo for another epic work trip! While I'm gone, here  is your bi-weekly fix of sage Chobot advice! This round, we've got bitchy women, a little bit of puppy-love and some potential cheating added in for flavor! Enjoy!

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Q: Jess,

I wanted to get your opinion about asking out people at work, and I don't mean people you work with but more people who work at places you go, i.e. bartenders, waitresses.  I've always through that this was a no go, but there is a girl who works at the veterinarian's office I take my dog to and I want to ask her out.  I go in every 2 or 3 weeks to pick up my dog's meds and I feel like she's flirting with me, but it could also just be her being nice to the customers.  What do you think? —JP

JESS: I don't see anything wrong with asking this girl out. It's not as if you work there, so that complication is avoided. True, the "flirting" you think she's shooting your way might actually be polite and proper customer service. Still, your instincts may be right! The best way to see if your dating Spidey-sense is correct without making yourself look like a moron is to keep your proposal for a tandem outing quick and non-aggressive.

Quick, because this girl IS at work and has a job to do. Nothing will get you rejected faster than by dawdling around, getting her in trouble and being generally annoying. Non-aggressive because if she does pass on your offer of eternal love, you don't want to feel like a loser every time you go to pick up your dog's meds from that point on.

Q: Riddle me this Ms. Chobot,

Most self-conscious at its most confident.
Most jovial at its most serious.
Most blind at its most awestruck.
And its greatest successes often end in its greatest failures.

What is it?

Anytime a guy cold approaches a girl, it's one of the most terrifying moments in life. Here's a secret -- while she's just sitting there, unaware of us -- we've already projected the possibilities of our success (whether it's riding off into the sunset or -BLEEPING- in the back of a Volkswagen). It takes so much courage (or alcohol) to start the approach that men pick their women and have time to think about her, obsess about her, and generally blow the possibilities out proportion. Whereas it seems, in this puzzler's limited male perspective, that women get to judge and pick the best of the male litter as we parade by with our best/cheesiest pickup line or a general display of awkwardness. Which brings me to my (unanswerable?) question -- Why do guys have to do all the work?

Let's face it, men and women are all looking for the same thing -- captured by your "there's always someone for somebody" catch phrase. A mature woman wants, in the end, a "good" guy, or at least that's what they claim. (Field research seems to point to that women end up with assholes -- whether consciously or unconsciously.) Rather than complaining about a string of crappy dates or a worthless boyfriend, why not try putting in some effort and sweeping a man of his feet? Oh, it's hard? It's horribly stressful? Welcome to a single man's Saturday night, Sister. If a beautiful woman (assuming beauty is some sort of placeholder for personality) is worth that struggle for a man, wouldn't a good man be worth that struggle for a woman?

So how 'bout it Chobot, ever try to woo a guy? (By the by, if you need pickup advice, don't ask your readers -- we don't know either…)

Signed,

The Relationship Riddler!

JESS:
-What is a big talker yet never talks?
-Who thinks they're the pursuer but is usually the pursued?

Answer: Dudes.

Ha! That's right! I accept your challenge and throw it right back at you! Why? Because it has been MY personal experience that almost all guys are chicken-shit when it comes to dating. If I ever want to get a date, I'm the one that has to ask the guy out. That's right- with the exception of one or two guys that I can think of, I've always been the one to pursue a relationship. This includes my ex-husband (who, by the way, I also proposed to...the first time...long story). Also, I'm often the one to make the first move (aka: kiss)!

So, Relationship Riddler, I ask you: what the heck is wrong with you guys? Grow some man-meat under that johnson of yours, stand up, walk away from your friends and ask that damn chick out!

Q: Hi Jess,

Love your column; it’s always really insightful and funny.  My question though, is no laughing matter; I desperately need your advice because I’m utterly confused.

I consider myself a good looking guy that has a lot to offer (funny, sensitive, etc..) but I have had limited success with women in my life.  I accepted the many rejections because I always thought that one day I would get what I deserved.  I finally found that special girl about a year ago, at least I thought I had, because unfortunately, I have doubts.  For the first 6 months, things were amazing; I was in love like a school boy.  But eventually, the temptation of other women started to re-surface.  I found that many of the women I always dreamed about having sex with (but never really believed it was possible) were now throwing themselves at me, and it’s driving me completely nuts.  Even though sex with my girlfriend is good, the temptation of cheating on her or of leaving her to pursue my other sexual urges is filling me with guilt.  I find myself thinking of other women ridiculously often, much more than when I was single.  I am asking myself if my love for her is just a sham of comfort and habit instead of the true uncompromising feeling that my idealistic self has wished for all of my life.

Is this just normal hormonal behavior for a heterosexual male or am I fooling myself by thinking I am still in love with her?  Talking to her about this will understandably freak her out so what should I do?  Please help! —Anonymous

JESS: Sounds to me that the relationship with your girlfriend is lust confused as love. Considering that you have had limited success with relationships up to this point, I can see why you have confused the two. It is also because of this previous difficulty with women that you are finding yourself so tempted now. It is the way of the Universe that every time you're "taken" everyone that has a vagina and walks within a 5 foot radius of you will suddenly need to jump your bones (note:vaginas are optional). By having so many women in heat hunting you as if you were the last male on Earth, how could you possibly resist?
Well, if you were really in love with your girlfriend, you wouldn't have any difficulty with it what-so-ever. See where I'm going with this?

My advice to you: If you truly want to avoid feeling guilty then don't cheat on your girlfriend. Either choose to break up with her or have an honest discussion with her about your desire to start seeing other people (and be ready for her reaction - good or bad....but probably bad).

Q: Hi Jessica,

During my 1st year in med school I met and befriended a 21-22 yr-old-girl who was in the same class as me.  We actually shared quite a few things in common: we both LOVED video games and we got along pretty well as friends.  We used to IM each other, complaining about classes/tests or talking about the latest/upcoming games.  And then a few times I'd hang out with her and play some video games whenever we had some downtime from studying.

I really liked her, and I was disappointed when she started dating another guy from school...I felt like I probably didn't act fast enough or take the initiative.  Despite that, I got over the situation, and we remained decent friends, until last fall.  I'm not sure what happened but she started to basically avoid me.  I tried to talk to her and she admitted that she was getting annoyed with me and trying to game with her so much; she even brought back every single game/game accessory I voluntarily lent to her.  Upon seeing that, I basically overreacted and we parted on less than amicable terms.  I sent her a polite and penitent apology message after we parted but she never acknowledged/replied.

Ever since then I have tried to move on, but living in a small town of less than 15,000 people and going to school where I see her almost every single day has been "nerve-wracking", to put it bluntly.  What's made it even worse is that she maintains a friendship with another student in the same school who i also used to be friends with (but somehow wronged too) - I introduced the two of them together to be friends, ironically. :-p  Not only that, but I'm moving to a much larger city for my rotations this summer, and not surprisingly enough, she chose (and matched) to the same rotation site :-p

With all that said, looking back I wonder if maybe I was too "one-sided" about the friendship.  I noticed that I always took the effort to try and get her excited about things, and she didn't reciprocate voluntarily.  Nevertheless, I often find myself trying to think exactly what I did wrong to deserve this.  I just feel trapped (literally and figuratively) for some reason, and I can't get any closure because of my semi-constant daily reminder of her, not to mention my ridiculously heavy workload of tests/classes/board exams.

Do I need to wait for the opportune moment to move on?  Or do something now?  Please reply. —DT

JESS: If you're being totally honest with me regarding your story then this girl is a MEGA-BITCH! You should be happy and thankful to have gotten her out of your life. F*^&k that chick, ignore her stuck-up ass and find someone cooler who will appreciate your friendship and focus on your studies. Nothing says, "Screw you, lady" then becoming a rich doctor :)

Q: Main question: Hey, I have this classmate of mine who showed a book that tells guys how to get beautiful women to bed.  Is there any proof that such books actually work or should I just work on my "A" game myself?

P.S.: I also think your very pretty and would love to spend a night with you .. but your ssoooooooooooooooo far away!

Also, what do you look for in a guy if he has nothing important or new to offer? (Like average joes..)

JESS: Oh wow. There is so much that's right and so much that is wrong in your question. I'm going to tackle them one at a time:

- I have NO idea which book your talking about. Therefore, I have NO idea if such a book "works." Based off of the PS you sent, I'm guessing that it does not and so you should stick to your "A" game...unless your PS is your "A" game, in which case, I suggest you read that book.

- Everyone has something interesting and special about them, even average joes. Personally, my requirement are that the guy has to have creativity, drive and intelligence. I don't care how hot they are, if there's nothing between their ears, they're worthless to me.

Q: Hey Jess,

A while back I was going through what seemed like a never ending string of bad luck with meeting women and as a result I have lost all self confidence in myself. It's been so long since I've had sex, that if someone could regain their virginity I would be the "30 Year Old Virgin". It feels as painful as it sounds! Nowadays, every time I want to talk to a girl I get so nervous that I can't even think of anything to start a conversation with, or I immediately think she would never be interested in me.

I've been thinking that I really need to see a psychiatrist or someone along those lines, but haven't because I feel to embarrassed about bringing this up with someone face to face. Please believe me, I don't want to just lie down and give up, but I don't even know where to start in pulling myself out of this downward spiral. Any advice you can give, not matter how brutal, would be appreciated.

Thanks in advance, R

JESS: I bet it IS painful! Blue balls for the LOSE! Seriously though, if the self-confidence issue is so bad that you've thought about seeing a psychiatrist then you probably should. There is NO SHAME in going to see someone to help talk things out. The way that I look at it is this: you are essentially paying someone for their educated opinion and advice. I've always thought that psychiatrists are MUCH better then asking family and friends because they'reun -biased, can give you a clear outside perspective and are forced by law to keep their mouths shut about anything you tell them (unlike your buds).

Chances are your story is NOT the worst one they've ever heard, so there is nothing to fear about going and talking to them face-to-face. Plus, the sooner you start, the sooner you'll start feeling better.

The toughest part of the psychiatrist issue is finding one you respect and get along with. It might take a few trial and error visits, so be prepared for it, but eventually you will find someone who will be able to help you get things back on track. Good luck to you and I hope you feel better soon!

Q: Hey Jess,

Well my situation is between college and my off-time. I'm a major geek. The problem I have is: I feel my friends are letdowns and school stress is getting to me. Should I just let go of my friends and bury myself in the books and hope for a better future?

Hopefully there was a legitimate question in there, I was afraid of going off on a long rant. Maybe you could give me some encouraging advice?

JESS: I think the answer to your problem can be solved with balance. Yes, your friends are probably losers but are they good friends to you? Yes, school is stressful but so is being poor and jobless. So, how can you make these two things work?

Answer: Time management.

If your friends are falling behind, then that's their problem. As long as they're not dragging you down with them I can't think of any reason to stop hanging out. Just stop hanging out as often. Spend that extra time hitting the books. With more study comes better grades. With better grades comes less stress and eventually (hopefully) a decent job somewhere.

If I had to guess, I would say you're probably burning the candle at both ends. Trying to squeeze too much play time and study time into one day. While you certainly can have both, you can't always have both at the same time. Learn and know your limits and organize your time accordingly.

Jessica Chobot is a lifetime gamer and zombie slaughterer. When she's not lovingly staring at her limited-edition, Japanese import Hello Kitty Dreamcast, she is a video host and writer for IGN.com and GreenPixels.com. Check out IGN Strategize, Jessica’s weekly video with tips and tricks to kick ass on your favorite games.