Letters To My Little Brother: Misadventures In Growing Older (4 page)

Me
: Doctor…uh…

PP
: Doctor who?

Me
: Haha! I like the reference. But no, not him. It was Doctor Spaceman.

PP
: From
30 Rock
?

Me
: Maybe? Cause if it were, then it’d be another esoteric-yet-hilarious pop culture reference.

PP
: Get out before I call the cops. Now!

As you can see, Squirrel, there don’t seem to be many good options when asking someone about their sexual history. Even if you do ask, though, who on Earth would tell you the truth? Wouldn’t anyone with an STD be too embarrassed to tell you? If you’re in the moment, do you really think someone would tell you they’ve got hepatitis, especially after they’ve let you get so far with them already? What incentive does a person have to be honest with you other than the kindness in their heart?

I guess the best advice I can give you is two-fold. First, make sure to get a blood test for STDs with your twice-a-year checkup. It’s a smart idea for both your health and the health of your potential intimate partners. Second, be up front with asking someone about STDs. It’s awkward for both of you, but remember that they want to know if you have an STD just as much you want to know about them. Have the conversation and get it done. Plus, if you have the conversation before you get intimate, it’s probably a good way of telling someone that you want to get it on with them like right-the-fuck now.

Before I continue further, I want to reinforce that questions such as those are all necessary to your well-being. It’s an unfortunate reality, I know, but it’s a reality nonetheless. Nobody wants to be in the position of revealing such personal details. Nobody wants to admit they have a drinking problem or that they had a child at the age of 16 or that they jerked off to anime porn. Once you get to that point of intimacy, however, these kinds of questions are both fair and necessary to ask.

Questions about things like sexting and the ensuing drama, on the other hand, are completely self-inflicted. You’re causing yourself an unnecessary headache for a marginal benefit. I only know this because I just learned about this sexting fad. I was hanging out with some friends when we had the following (only semi-fictional) discussion:

Me
: Yes, I do find her quite an attractive partner, both on both a physical and emotional level.

Jethro
: Have you gotten any naked pictures from her yet?

Me
: Pardon me?

Jethro
: Naked pictures. Of her.

Me
: I would never, ever view or request such demeaning material.

Jethro
: Dude. Has she sexted you or not?

Me
: Does Snapchat count?

Jethro
: No.

Me
: Then no.

Jethro
: Wait – she sexted you over Snapchat?

Me
: No, I was just clarifying the question.

I’ve come to discover that sexting is kind of a real thing. People (other than just Brett Favre) actually send other people pictures of themselves naked! The fact that people put their private parts out there for (potentially the whole) world to see doesn’t surprise me. Sexting blows my mind for some other reasons:

• People actually find awkward selfie pictures sexy.
  
• People actually find ways to make awkward selfie pictures sexy.
  
• People do this enough that it has its own word.
  
• People do this enough that it is commonplace.
  
• And, last but not least, if this is such a commonplace thing, then why hasn’t anyone ever sexted me????
  

Now that I look back on it, I know a lot of people who claimed to have sexts on their phones. Boobies, fellatio, full-frontal shower shots, etc. I’d find that weird, but a lot of those guys also had pictures of their largest poops as well. I also did some “research” on the subject and (re)discovered GoneWild, a sub-Reddit full of girls taking naked pictures of themselves and posting them online. (Then again, it could be their jilted boyfriends posting the pictures. Who knows?) There really are a lot of people into telephonic voyeurism. Interesting.

That all being said, I’ve never met a girl who claims to have a sext on her phone. Is this yet another form of sexism? Do girls not want to see naked dudes pop up on their screens during class or work? Or do they not find penises [I was going to write ‘peni’ but apparently ‘penises’ works with spell check] attractive enough to request pictures of them? Or is it something else entirely? Clearly I have a lot of questions. Lemme think out loud for a second.

If a girl sexted me, would I sext her back?

I’m not that selfish, but still…It depends. Am I dating her?

Does it matter?

Yes.

Sure, say you’re dating her.

Only if she asked for it.

And if you’re not dating?

Can I use pictures of someone else’s junk?

You realize that means you’d have to Google “someone else’s penis,” right?

I feel like that’s a fair tradeoff.

How do I even ask for a naked picture?

I assume you use some combination the words “please,” “send,” “me,” “a,” “naked,” “picture,” “of,” “yourself.” You can figure out the order.

I clearly hadn’t made much progress towards sexting. So I decided to consult my sensei, Jethro, once more. Here’s a recap of our conversation.

Get on Skout or OkCupid. Bombard with messages anyone who has a high response rate. When they engage you in conversation, lie your ass off. Once you receive a sext, you have three options: ask for more, cut off communication entirely, or send a text saying, “lolololololol u just got trolled!” and then cut off communication entirely.

I’m not sure I could do any of that. First of all, I’m not that mean. I have a lot of personal flaws, and being vicious to people can certainly be one of them, but never could I completely and totally deceive someone solely to see a blurry, pixilated image of them naked. Second…well there is no second. I’m just not committed enough.

Jethro went on to describe how he has a grand total of 55 pictures of naked girls on his phone. 55!?!? That’s like…55 girls! Fifty-freaking-five! He even talked about how he’s received naked pictures of his girlfriend’s girlfriends WHILE they were dating! What the fuck?? What is that thought process?

Boyfriend
: Wanna send me a picture of yourself topless?

Girlfriend’s Girlfriend
: But you’re dating my bestie!

BF
: Exactly. Clearly that means it’s a purely scientific exercise to examine the aesthetic value of your physical form. I’m only attracted to one and only person: your bestie. I obviously have no ulterior motives here.

GF’sGF
: Yeah. That makes total sense. She couldn’t possibly be offended by a science experiment! So a topless pic then?

BF
: Let’s go full-frontal while you’re at it. Just to be on the safe side.

GF’sGF
: Awesome. Check your iOS or Android device!

Jethro also coached me on the proper process. He said, once I feel confident enough to ask, to say, “Wanna sext me?” When she responds, “What??” then you respond with a winky face ;-). If she’s not comfortable, she’ll think you’re joking. If she is, you get the goods.

Clearly I’m a little behind on the times. I’m not a prodigious philanderer, let alone a talented sexter. I’ve met a lot of girls in my life and since none of them have ever sent me a naked picture, I have to assume it’s something wrong with me. I’m betting it’s the lack of hair around my nipples or my gaunt frame and pointy hipbones.

I guess some of us are just destined to live traditional, boring, sext-free lives. And by us I mean me.

No matter what, I want you to realize that you are not alone in asking these kinds of life questions. I know inner quarrels about your place in the universe are a little heavier than wondering how to politely ask for nudies, but please recognize that any question that keep you up at night is relatable. Don’t be afraid to ask yourself about what it means to be a better person. Don’t be afraid to ask a partner about their sexual health. You may worry that they’ll scare off the one nice girl you’ve met in God-knows-how-long or something, but don’t let that terror get the best of you. There are mature ways to handle these talks. I just haven’t discovered them yet.

Peace, love, and all that jazz,

-Big Boy

CHAPTER Four:

How Not to make friends

Dear Squirrel,

You may be surprised to hear this, but I’m not very good at meeting new people. I genuinely believe that I interact with new people better through my writing than if I met them face-to-face. It’s not that I’m shy or anything. It’s that I don’t know what to say. For a goofy mug like me, speaking to strangers can be challenging, especially getting past the part where I will undoubtedly mention, “Yeah, I wear boxers that say ‘Kiss Me’ and I live with my parents. I also know some people who poop and then immediately jump into the shower without wiping, but I wipe anyways. I fold my toilet paper, by the way. I’m a folder. Nothing but four-ply touches these cheeks.” With witticisms like that, you can clearly imagine the kinds of friends I attract.

Starting out in college, for example, presented a number of obstacles for me. Specifically the partying stuff. In case you haven’t already figured it out, I don’t enjoy confined spaces, alcohol, and sweaty people. I had to come up with a system in order to expand my social presence. Here were my do’s and don’ts of partying:

Do:
Fuck Shit Up

Saying outrageous stuff really gets people psyched. Just yell, “Let’s get involved!” or “Let’s get reckless!” or “Let’s fuck shit up!” and people around you will go straight-up bananas. If the witching hour is close at hand, you can add in declarations of love, but I recommend holding off on that one till you’ve passed Partying 101.

Don’t:
Fuck Shit Up

Don’t literally fuck shit up. Then you’d have to pay for the newly-fucked-up shit.

Do:
Small Talk

As I said, I literally have no idea how to do this. I’m just saying that you need to know how or else you’ll end up being a party-going disaster like me. I once had a lovely young lady beg me to go to a club with her and her friends. She kept emphasizing that she’d do
anything
to make me come with her. Well, needless to say, I didn’t go the club because a) I am an idiot and b) because I had no idea how to hold a conversation with her once she stopped laughing at my
Power Rangers
shirt.

Do:
Wear a
Power Rangers
T-shirt

It’s a great conversation starter.

Don’t:
Tuck It In.

Enough said.

Do:
Make An Effort

I may not drink, but I have an awesome BFF who taught me to play Flip Cup at a few of her parties. Sure, I kicked ass because I had been stone cold sober for 23 straight years, but only because I put myself out there and learned how to enjoy alcohol-centric events. I made an effort to join parties on my own terms and I was lucky enough to have a friend/friends who were willing to accept me for that. You have to be willing to squeeze if you want to get the juice, or something like that.

Don’t:
Be the Tall Awkward Guy in the Corner of the Party

That’s my job. I need it. In the end there can be only one. Highlander Theorem, remember?

Do:
Say How Much You Love This Song

Don’t:
Admit How Overplayed and Annoying It Is

Do:
Push Your Comfort Zone

Rule Three states that we are “in it for the lulz.” That means if you have the option of hitting up the largest nightclub in Africa or going to bed early, you should go dance your face off. If you have never gone to a semi-formal or a horse race or a midnight movie premiere, then try it out. You’ll never grow without spreading your roots. Take calculated risks. I grew closer to one of my all-time favorite people when he and I hit up a Latin-themed bar in downtown Rabat, Morocco. He was a maniac that night and thought it’d be funny to give my phone number to an (ambiguously gay) Moroccan drug dealer. What does this have to do with pushing yourself? Because over the next few days, every poorly-translated, semi-flirtatious text I received about unwanted narcotics made us laugh even more. We bonded because I put myself out there (and inadvertently became the subject of a few super awkward international telephone conversations).

Don’t:
Let Other People Push Your Comfort Zone

If your friends are smoking hash in your room and you don’t want any part of it, then don’t be part of it. If your girlfriend is kind of tipsy and wants you to take that big next step (yeah,
that
one) and you don’t think it’s a good idea, then don’t do it. It’s your life, man. Don’t do anything you’ll immediately want to take back. Only do dumb stuff if you’ll be able to laugh about later. If your friends or loved ones won’t accept you, your principles, or your hesitancies, then I highly suggest you take the painful step of reconsidering why they’re your friends.

Do:
Give hugs.

Hugs are important signs of affection. They magically make you go from being “just Facebook friends” to “people can text and it won’t be weird or awkward.” You can give your bros some one-armed hugs a la the great Mark Titus. You can send messages through hugs (like, giving a girl a one-armed hug means you are intentionally not providing an opportunity for
The Look
.) You can get that soulful, warm, fuzzy fulfillment that only human heat can provide. I know you’re a bad hugger, but trust me: It is never a bad thing to be called a good one.

Don’t:
Use Pirate Pick-Up Lines

Wearing an eye patch and declaring, “Are you buried treasure cause I be digging your chest?” will never, ever work. Ever.

Partying is not the only method of alienating people, however. You can also do that by screwing up all your romantic passes at the girl(s) of your dreams. The easiest route to doing so is through college date functions.

In my mind, the three worst things about college are (in order) binge drinking, intermediate econ, and date functions. I’d consider research papers a close fourth and group projects a distant fifth. Unlike the others, though, date functions have the potential for creating life-long memories of the tragi-comic variety.

Take, for instance, one date function in my sophomore year. A girl in my theater class asked me to her semi-formal after having spoken to me all of 3 times. She must’ve thought I was way cooler than I really was because of all the snarky, self-deprecating remarks I made in class (my sophomore year in college was a lot like my sophomore year in high school in that sense…). She was the only one that laughed. She even tracked down my room one night after I’d said — in order to avoid an after-class dinner with her — I was going to be watching
Pushing Daisies
. She awkwardly sat on my bed while I desperately avoided the dynamic duo of conversation and eye contact.

Anyways, she eventually asked me to her semi. I was too nice to say no. Come the big night, I stood around silently, a phony smile painted on my face, and nodded approvingly every time she said something. She kept making me dance with her (probably to avoid the long, LONG pauses in our discussions), which proved difficult because of our immense height differences. As we swayed/“grinded” to Lil Jon or the
Aladdin
soundtrack or some shit, I wondered which would happen first: my knees chafing on her backside or my genitals accidentally swinging forward and bopping her between the shoulder blades.

Lucky for me, 2am arrived quicker than usual, thereby leaving me with the eternally awful task of saying good night. I not-so-subtly hinted at my disinterest by offering her a one-armed hug in the parking lot. It’s not like she could’ve leaned in for a kiss anyways. Without a step stool, her lips would only have found the underfed ridges of my ribcage. I didn’t even walk her back to her door. Needless to say, I’m not sure she ever spoke to me again.

Let’s get back to you. It’s your date function, which means it’s your responsibility to ask someone. Yes, YOU have to ask someone. You got off easy when that girl asked you to prom junior year. Not this time. People probably won’t razz you too bad for showing up alone, but you will hate yourself for third-wheeling (literally) everyone else. I asked a girl (who I was really into) to a date function my freshman year, but she had her own semi-formal that night. We both went alone to our respective events. (I’m not sure if that means she wanted me to go to hers and therefore didn’t ask anyone else, or if she just couldn’t find a date. She was pretty and popular, and I’m arrogant enough to believe that the world revolves around me, so I’m going to go with Option 1.) I’m not sure I remember a moment so lonely in my entire freshman year. I watched all of these beautiful couples disappear one-by-one into the gardens to hook up beneath the pale moonlight while I stood solitary in a boozy, mostly-empty dance hall with all the kids who were either too miserable to make out or who dropped acid and wanted to watch the spin lights. I arrived at 10:15 and left by 11. I spent the rest of the night playing Xbox in my shirt and tie. Don’t let that happen to you.

It’s important to know who you’re asking and what it implies. Are they a friend? Is it clear that you want to stay friends? Are you trying to tell them you are lonely and that you think ‘bears gotta eat’? Are you asking someone as a real, bona fide date? Here’s an example. One of my favorite people on Earth asked me to go kegger-skating (roller skating while drinking) since her boyfriend was too busy to go with her. It was an amazing night. We chatted with her friends and skated and laughed. Awesome time. Fantastically wonderful. My best bud (let’s call him Bobby, just to spite him) was asked to the same date function by one of his classmates. I think the girl that asked him was in a long-distance something or other that left the ethics of her sexual fidelity in a vague grey area. Either way, they got very drunk and very handsy. I kept encouraging him to make a move. He did…by falling, pulling her down to the rink, and breaking her wrist. So choose wisely, Squirrel: your actions can have consequences. Don’t pick a date with poor balance.

No matter what, though, you’ll do fine. Date functions are about having fun regardless of who you go with. You’ll be with making mischief and madness with your friends whether your date is a spud or a superstar. Just be sure to temper your expectations of your date. It’s not prom. It’s not the end-all and be-all of your personal life. And especially be sure not to expect too many fireworks afterwards. I once stayed up till 2am — persevering through sleep deprivation and a beer-infused rush party — because a lovely lady asked if she could spend the night with me. I was super into her, so of course I said yes and immediately tried to make a move once she climbed in bed with me. You know what she said? “I’m so glad I have a friend like you who I can sleep with and won’t pressure me to hook up.” I rolled over and didn’t speak to her for the next week out of shame, anger, and pure embarrassment. As I mentioned earlier, be aware of the implications, both for you and for her. Just cause you think it’s a date doesn’t mean that she does too. Stay in the moment, have fun, and stay safe. That’s the most any of us can ever ask for.

You should also be careful what you say during these early phases of friendship. While you know I also encourage honesty and openness, sometimes that strategy can be overwhelming, even when it’s used on me.

Look at the time I signed up for Christian Mingle. Yes, you read that correctly. My friend said he had good success with JDate, so I figured that maybe I’ll have success finding some new leads on Christian Mingle. Let me tell you, Squirrel: NEVER SIGN UP FOR IT! Jesus H Christ. After skipping past the sections about the site’s official worship statement, and after taking offense that there were no selection options for my friends in the LGBT community, I decided to do a basic search. I clicked the following (highly generic) options:

• Lives within 25 miles of me
  
• Age 22-25
  
• Doesn’t smoke
  
• Hasn’t been married/divorced
  
• Does not have children
  

Do you know how many people popped up? EIGHTEEN. That’s right. 18. One. Eight. Eighteen freaking people. Is this a trap? Was there a conspiracy of divorced Christians with kids baiting me with promises of curing my romantic loneliness? And because everyone on these sites lies about themselves, what’re the chances that at least of those eighteen is actually divorced and/or a parent? What are the chances that I go on a date with them?

How do you handle stuff the possibility of meeting one of these people in a mature way? I’m serious. Even though I can think of all my major dealbreakers, I’m still unsure of how I would express that I’m no longer interested in a person after one or two dates. Like what if your date checks her phone during dinner, glancing at it before rolling her eyes and tucking it back in her purse? What if she’s like, “Oh, it’s just my ex-husband. He’s making sure my kid will be waiting for him in the driveway at 9am”? How do you respond? Do you do the ol’ dine-and-dash? Do you pretend to choke to death on your food and then, once in the ambulance, tell the EMTs the whole story and thank them for sparing you embarrassment? Or do you just play along normally and ignore all communications with her from then to eternity? I’m partial to Option #2, but I can see how the others might be more appealing.

Can’t you see how all this friendship stuff can get so messy so easily? And none of this includes comprehending all the different categories of friends. Acquaintances, people you see on the way to class, Facebook friends, real friends, good friends, friends you share your feelings with, friends you have lunch with, best friends, etc. There usually isn’t any specific demarcation of these friendships. You just seem to know when someone transitions from one category to the next. Maybe it’s cause you climbed onto the roof of the student union together. Maybe it’s cause you hung out a lot and explored the bowels of the library after it closed. Who knows?