Welcome back to "Ask Jess, Dammit!"
Just so all of you know, I'm currently writing this article from a hotel in Shinjuku, Japan. That's right! I'm half-way around the world, in the midst of my vacation and what's on my mind? Your dating (or, lack thereof) woes. If that's not passionate dedication, I don't know what is! However, with that being said, today's article is going to be reduced in size. One, because I don't know how long this internet connection is going to hold out and the LAST thing I want to do is end up struggling to type this in some otaku internet cafe (although they do give you free drinks and corn soup...so it's not all that bad); and two, because I want to hit up Akihabara, chill at a maid cafe and buy a few robot figures.

I knew you'd understand.

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"I'M JUST A SUCKER WITH NO SELF-ESTEEM"
Q: Have you ever struggled with low self esteem or been really self conscious or put yourself down even though you know you could succeed? If so, how did you overcome it, if not, how would you? —C

Jess: I certainly have struggled with low self-esteem. In fact, I still struggle with it, although I do think that the fight gets easier as you get older.

Back in the day (read: sixth grade and up), I was very shy, gawky, and majorly zitty during my pre-teen years. Gawky, I grew out of. Shyness, I overcame out of pure necessity. Zitty, ah, zitty still plagues me a bit. I remember in middle school having such a bad breakout on my forehead that one woman who saw me asked my mother if I had chicken pox. I became so self-conscious of my skin and its daily bouts with hideous abscesses that I would actually fake sickness so I didn't have to leave the house, or, if hiding away wasn't an option, I would style my hair in such a way as to attempt hiding the afflicted area.

At some point, things got so bad, I asked my mother to take me to a dermatologist. While it improved my situation, it certainly didn't "clear" the problem up and my complaints from that point on were often met with a resounding, "You'll grow out of it."

"Growing out of it" didn't really happen until my sophomore year of college. Even now, I get what I call "period zits," or super deep blemishes that hurt like hell and come roughly around the same time as my period. This makes working in front of a camera, or being in a public setting such as E3 or San Diego Comic Con, much more difficult since I now work in an environment where thousands of people can see I have a volcano on my chin.

It friggin' sucks.

So, how does one overcome it? I would say you should try to be as proactive as you can. Look for solutions to whatever problem you feel is hampering your self-esteem. In my case, it was the awkwardness of going though a major ugly-duckling phase. I took as many steps as I could to improve the situation but in the long run, I just had to accept the fact that I was doomed to struggle through it on my own accord. Also keep in mind that the struggle might last a long time because self-esteem just doesn't fix itself overnight. If you feel as if you're a strong enough individual to tackle your issues on your own, then go for it. But, keep in mind that it's not a bad thing to look to outside sources. A trusted family member or friend can be a great source of reassurance and guidance. If you would rather go to an outside source, then don't be afraid or ashamed to look to a professional counsellor.

"But I'm a creep, I'm a weirdo..."
Q: Jess, Do you have any tips/ideas to look like less of a creep around women?  I feel like I've gotten past my whole "no one loves me" phase and now I'm perfectly willing to accept being alone the rest of my life.  The problem is that general relations between me and the fairer sex are still very strained and awkward.  While I seem to do adequately in small talk over the Internet, verbal exchanges fall apart in one-on-one settings.  It's like I'm either the sexiest man alive (highly doubtful) or a deformed troll (not as doubtful). Females just come off as strangely fearful and defensive, which then puts me on guard and I start acting weird.

When I graduate college I'll be forced to interact with women in some capacity at whatever job I'm going to have. I need to get rid of this bizarre pattern of communications and find some way to just seem nice and friendly.  I'm told that I can be pretty funny, but that doesn't matter if you're playing to such an icy front. I really do just want to be friends. Suggestions? Thanks, Andy.

Jess: Andy, I think the real problem here falls into two categories. Number one: Your comment about accepting the fact you might be alone for the rest of your life screams volumes. You haven't even reached college and yet, you already think you're doomed? That's ridiculous! You're tossing in the towel now and giving up the fight!? If that is your attitude, then yes—you probably will end up alone. Methinks you might have a little bit of what's going on in question No. 1. My suggestion is to change your outlook. Keep in mind that there is always someone out there for somebody. You might not find that person tomorrow but you will find them. That's when the real struggle starts. You see, Andy, the real issue with relationships isn't finding the person but what you need to do to keep them.

As for the second part of your conundrum, the whole "talking to girls" thing, I think you might be over-thinking it. There's no reason why you should be changing yourself in order to attract a female, let alone converse with her. If some chick you're chatting up just isn't down with your flow, move onto the next one (that's where that whole attitude of, "there's always someone for somebody," comes into play). This isn't to say you should be a cold, callus, unfeeling bon vivant of the women-folk. It just means that you shouldn't stress if you try to be nice and are met with a cold shoulder. Chances are, she wouldn't have been someone you wanted to be with in the first place. 

"You've Got To Lick It...Before You stick kick It"
Q: Dear Jessica,

As a long time fan of your blogs and Preacher-Teacher, I am very excited to see that you have another chance to give us readers some love advice.  Anyway, I'm currently a college student and my lady boss at the clothing store I work at is cute as hell.  Would it be wise to try to get into a relationship with her, or would it be awkward beyond belief?  I really get the vibe that she doesn't have the same kind of feelings for me, but I haven't really talked to her a lot.  So, would it be wise for me to start?  I really want to know what you think.  If you could help me out, I'd give you fist bump—if that's still a cool thing to do.  Thanks for reading this. Sincerely, Lovestruck by boss.

Jess: I know the common and easy answer is the old adage, "Don't sh*t where you eat," or something like that. The point I'm trying to make is that I'm fully aware that most people would tell you not to do it.

If this job at the clothing store was your career path and the end-all be-all of your future employments then I would say, "Definitely, 100 percent DO NOT try and stick it in her." However, I'm hoping that you acquiring a college education means you are shooting for bigger and brighter things, in which case, your current job is only temporary. If this is so, then I say by all means, 100 percent try to stick it in. Good luck to you, sir.

"Everybody's cheating on the one they love..."
Q: Hi, Jessica.

Recently I threw a keg party at my house and a friend showed up with his girlfriend, who's cute and has a great body.

Of course, late into the night everybody was thrashed including my friend, his girlfriend and me. She then came onto me when he wasn't around and propositioned me with sex. I was very hesitant at first but naturally, the alcohol won the battle. I took her into my room and screwed her silly for hours. It was some of the best sex ever, and she wants me to come over more often while my friend is at work. I feel like a piece of dirt, but at the same time I didn't instigate it and the guy, my "friend," is actually a total asshole. The few people I've told about the matter actually congratulated me for fucking her, saying he deserved it. But I still feel like a prick, and now I'm freaking out because we're all supposed to hang out next weekend. I'm quite sure that we'll hook up again, especially if we drink, and I don't think I could control myself. So...am I the asshole here? Is it his fault for not satisfying his girlfriend, or is it her fault for cheating? Is it even worth all the trouble? Thanks!

Jess: Dude. You are so EFFED.

"WHY CAN'T WE BE FRIENDS?"
Q: Jessica,

Perhaps my question is a little different... being a married man, I'm not looking for a relationship, yet there can be a very thin line between friendly conversation and flirting.  My new job places me in a position where I work very closely with women.  It’s important to be good friends with one’s fellow coworkers, but a work environment can make the ice on which you tread VERY thin.  I struggle with this, often coming across as a bit of a bore at times because I play it safe by keeping everything about work.  It’s not easy to make friends by being a bore…so how can I compliment a woman and bring out my personality without coming across as a flirt? Some things are obvious, but how’s a guy find a balance down the line? Got any advice? —Joe

P.S. Congratulations on the new column, J. I hope you enjoy it.

Jess: Thanks for the congrats Joe.

In answer to your concerns, how you're handling your current situation is the right one. While it's always a wonderful thing to be relaxed and have fun at your job, keep in mind that it is still a work place and not a place where one is supposed to make friends. As for the flirting, again, I think what you're already doing is key. You are your own best gauge. If you start to feel uncomfortable about a certain situation, then that is your inner alarms telling you to back-off. Listen to them. Also, if you're unsure and do not want to seem overly stuffy, another good way to assess the situation is to exchange places with your wife. By this, I mean, if your wife were in a similar job situation where she was forced to interact with male coworkers, what level of her flirting would you find unacceptable? Keep the knowledge of what would hurt your feelings in mind when you find yourself in a similar situation.