Things I’d Tell My 20-Something Self – Part 3

I don’t know about you guys, but birthdays always trigger a lot of self-reflection for me. I turned 36 a few weeks ago. If someone were to ask me what I like best about being in my mid-thirties I’d say the clarity. It’s nice to look back and be able to identify everything you’ve grown out of. So, in honour of birthdays and hindsight, I thought it was time to share some more things I’d tell my 20-year old self (you can check out the full series here.)

It’s never too soon to learn about good alcohol

Fifteen years from now you’ll be sharing some Pinot Grigio with a ridiculously handsome man. You’ll hold up the bottle of Masi (a wine which was introduced to you by another man that you once found charming circa 2001and tell him, “this is the only good decision that came out of my years of drinking as a 20-something.” You’ll be 180% right. I know the urge to try things just for the sake of trying things is strong this decade, so I’ll just cut to the chase:

The pink bottle of $4.99 “strawberry wine” you keep passing at the liquor store on the way to the cooler aisle tastes exactly as terrible as it’s neon packaging suggests. That non-FDA approved liquor your friend brought back from Israel will make you black out. And throw-up. Then black out again. It will also make your friends simultaneously black out and throw up. Any drink with Red Bull as an ingredient is sure to make you jump up on furniture (which sounds kind of fun now, but it’s something you’ll grow out of. Trust me.) Drinking on the subway is hilarious, but it’s not classy. Southern Comfort is awful. Stop treating your Friday nights like you’re Janis Joplin on an epic bender. Instead, drink the Masi. Always drink the Masi.

The “one that got away” is a myth.

They didn’t “get away” – they left you. It sucks and it hurts and you’re going to cry over these people, but it’s for the best. I promise. Have the feelings you need to have and then move the fuck on. Don’t waste time obsessing over or longing for people who simply didn’t choose you. They. Didn’t. Choose. You. (Keep this in mind when these people resurface requesting a second chance.) Spend your time loving the people who have chosen to be in your life. Start with yourself.

Expect more from the people you date.

As a 20-something you joke that your dating motto is, “have low expectations and you’ll always be pleasantly surprised.” You adopt this line of thinking after a series of breakups and disappointing sexual encounters – both wanted and unwanted – leave you heartbroken and confused. You start asking for less, when really you should ask for more. Don’t do this. You should expect things from the people you date – like, respect, honesty and integrity. Be picky. Ask for what you want out of relationships. It might mean that you spend more time alone, but it won’t matter in the grand scheme of things.

Learn to be still.

I know it’s hard. You live in a city of 5 million people and around every corner there’s something or someone new & shiny to distract you, but please try. Stop focusing on things and people that don’t serve you, just so that you won’t have to be alone with your own thoughts. The only way you’re ever going to feel at peace with yourself is if you face your problems head-on and deal with your personal shit. Don’t wait until the end of the decade. Begin early.

What would you tell your 20-something self?

Things I’d Tell My 20-Year Old Self #16 – Joshua

joshua pompeyToday’s instalment of Things I’d Tell My 20-Year Old Self  comes from my friend & online dating expert, Joshua of JPompey. Check out the rest of the series here.

Dear twenty year old Joshua,

Right about now you are walking the streets of Downtown Albany, probably drunk, trying to live it up in your final year of college.  And while I can’t argue that you have come more into your own this year than at any other point in your life so far, we really need to sit down and have a chat about how you could go from making this one of the best years of your life, to being an all-time, legendary year that drunk college students for generations will want to emulate.  Are you ready for this?  You might want to sit down for a few moments.

1.  For Christ sake, take those damn jeans off and get it together!

Seriously dude.  You dress like an absolute clown.  Your jeans are five sizes too big.  They are shredded at the bottom.  And your t-shirts could fit at least two of you inside.  You are in shape for someone who drinks a thirty pack a week, you go the gym, and you have a nice body, so for crying out loud, take a woman to the mall with you, charge a few pairs of skinny jeans before the Brooklyn hipsters steal your thunder one day, and invest in looking like you don’t need your mommy to come to Albany to help lay out your clothes.

2.  Keep your mouth shut when you hook up with someone.

I know you are insecure.  I know sometimes you wonder if the whole world secretly thinks you rarely ever get to see the Golden Palace of the Himalayas as you strut your wanna-be macho self around the city.  But on those rare occasions where for some absurd reason a girl actually wants to take off those over-sized, baggy shredded jeans of yours, don’t start telling every single friend you know that you gave a girl really mediocre sex last night.  You may get fake props, but women will find out and tell all their female friends to blacklist you from the, “I’ll go home with any guy after five drinks,” community.

3.  Cough up the extra few bucks.

I know you are poor.  I know you think you are so insanely cool for buying 30 packs of Keystone Light and “The Beast”, a.k.a., Milwaukee’s Best every week.  But the internal damage you have done to yourself from all those beers no longer allows me to eat oversized Pastrami sandwiches without popping several Tum’s, downing Pepto Bismal, and listening to Mumford and Sons to calm my nerves.  Be a baller and cough up the extra ten bucks for something classy, like Bud Light.

4.  Have the foresight to invent the world’s corniest shot.

It will taste like crap.  It won’t make sense.  And it will make you feel so lame when you are my age.  But one day, at least once during every party you attend, some lame guy will take out a bottle, yell, “FIREBALL SHOTS!” and make everyone at the party take at least one.  You won’t have a choice.  You’ll just have to suck up this lame excuse for a whisky that tastes like a combination of whisky, Big Red gum, and dying souls.  This trend seemingly will not go away, so while you still can, figure out the recipe that is currently in the works and get rich.  We will toast to our success one day with a Jagar Bomb.

5.  Be more confident in the bedroom.

I don’t know if anyone ever told you this, but you have the world’s biggest hands.  Apparently you never new just how lucky you were until years later.  So stop being such a sissy worrier in the bedroom.  Sometimes when you drink 25 beers in a night, your junk stops working.  That doesn’t mean you have to carry that fear to the next time, seven months later, when it only took you 8 beers to work up the courage to get a girl in bed.  Have confidence and show why you wear such big gloves in ways that will be remembered forever.

About Joshua – 

For some amazing free advice from my current self, where I have been helping online daters to succeed at a rate of over 99% since 2009, men, read this article now on how to save over $5,000 and 500 hours.  Women, read this free article to view actual profile examples.

What would you tell your younger self?

Things I Would Tell My 20-Year Old Self #15 – John

Hello Skinny Dippers! I’m working on book stuff today, so my friend John Drake has kindly volunteered to step in with the next instalment of the Things I’d Tell My 20-Year Old Self series. John is my former writing partner, a fellow motorcycle & sex/dating/relationship enthusiast and one of the best dudes I know. I hope you enjoy reading John’s advice! Stay tuned for more dating updates, reviews & other goodies coming later this week!

IMG_4730During my last annual exam, my Doctor asked for clarification of my age as she flipped through my medical file. She laughed as I responded, “Do you mean in birthdays, maturity or mileage?” While I may not feel as sprightly at 33 as I used to after indulging in more than a few Old Fashioneds the night before, in my mind I am still 20 years old.

That was, until the trajectory of my life journey recently placed me in close proximity to actual 20 year olds, at which point I felt as wise as an owl and old as dirt. After being made instantly and viscerally aware of the stark contrast between the limited worldview of a vicenarian (20-something), I began to ponder if I was ever that immature and clueless, or whether current 20 year olds have just been pampered to the point of having far less intellect and life experience.

I may have found myself giggling like a schoolboy at the supermarket just last week when I came across a package of Hung Wang Asian noodles, however I also have RRSPs in the bank, I own a vacuum, pay my taxes on time and don’t have to be told to floss – all hallmarks of maturity in my books.

Just as I wouldn’t tell my six year old self that Santa Claus doesn’t exist, there is much that I would leave a mystery to thirteen years my junior John. I would most certainly leave out specifics; the who’s, the what, the where’s – all of the decisions I have made, even the poor ones, have taught me valuable lessons that I wouldn’t trade. What I would change however, are the times I hurt people I cared about or who cared about me, regardless of whether it was intentional or not. I would also like to set him up for a higher level of success, learning from my mistakes rather than from the School of Hard Knocks.

In that vein, I would offer my 20 year old self the following counsel, in no particular order.

Be Honest

The importance of honesty was instilled in me at a very early age. It was held in high regard, paramount in fact, among other honourable virtues like courtesy, ambition and cleanliness. While I have rarely been intentionally dishonest, we’ve all told little white lies or lied by omission. It may have been innocent, or possibly ignorant, but I know for a fact that I have inadvertently led more than one girl on in my life by not being honest about my intentions or where I saw the relationship going. One lovely girl in particular, who I considered merely a nocturnal recreation partner, unfortunately saw monogamy and likely matrimony in our future and I never did anything to convince her otherwise. Be honest with the people around you, but more importantly, be honest with yourself.

Don’t Waste Time on Fake Friends

Friendship is not easy and it is a two-way street. Even as you get older it can be difficult to discern which friends will stand the test of time, or which ones shouldn’t. When you are young your friendships are based on proximity and musical taste, but life gets far more challenging as years go on. I was convinced that I would have been the best man at my best friend from highscool’s wedding and yet by the time he tied the knot I wasn’t even in attendance at the ceremony. You will experience ups and downs. The friends who help lift you up when you’re down are the ones you want to surround yourself with. Your friends will become your family and your benchmark for success, so choose wisely.

Nobody Has It All Figured Out, Follow Your Own Path

Some people wait patiently until mid-life to freak out about not having their shit together, but on the eve of my 25th birthday I had a full-blown quarter-life crisis. Witnessing many of my friends lock down solid jobs, condos and investments had me reeling with self-doubt about following my unique and less financially lucrative career path. One such friend who was in attendance at that 25th birthday has achieved perhaps the most financial and material wealth of anyone I know. He recently admitted that he was miserable at work and was jealous of the freedom, experience and flexibility I enjoy in my work. It doesn’t matter how big your TV is or how many bedrooms you have, you won’t be happy if you aren’t fulfilled by your work. I’ve made a great salary and I’ve made peanuts, but I always followed my passion.

Respect Your Parents

Age and experience often bring perspective, which in turn provide context and greater understanding. But as my old man has said on several occasions, “Learn from other people’s mistakes, you won’t live long enough to make them all on your own.” You share common genetics and ancestry, learning from their experience and about your roots will serve you well in the future. Whether you learn a family recipe, not to put gasoline in a diesel car or that you happen to have a predisposition to certain health issues, listen to your parents’ lessons and respect the sacrifices they have made in order to conceive, raise and support you – through colic, childhood, adolescence and beyond.

Take Good Care of Your Body

Education is wasted on the young. Unfortunately, so too is the innocence and stupidity of youth.
Your body is by far the most amazing tool you will ever encounter but much like any appliance it requires care and maintenance. I wish I’d worn earplugs to loud concerts, I wish I had applied sunscreen more often, I wish I’d never tried smoking or eating fast food. These things don’t make an impact when you’re young, but they compound exponentially over time as you age.

Live Within Your Means

It wasn’t until very recently that I became even mildly financially responsible. I bought a sports car and a new motorcycle before I paid off my student loans, I used my credit card like an ATM and I took vacations I couldn’t afford. Long story short, I placed a higher priority on things than I did on experiences or peace of mind. If I was to do it all again with the information I have now, I would have been more frugal and enjoyed the simpler things in life.

The reality is that I could spout off advice until the cows come home, but I can say with complete certainty that 20 year old John wouldn’t have listened. He was invincible. Immortal. Unstoppable. With age, experience and opportunity comes pain, politics, cynicism, regret and self-doubt. Sometimes being an adult means carrying the weight of the world on your shoulders. I wouldn’t want to trade places with my 20 year old self and I feel like I have a great deal of valuable information to pass on to him, but something tells me he could teach me a thing or two about perspective as well.

 What would you tell your 20-year old self? 

Things I’d Tell My 20-Year Old Self #14 – Akirah

It’s been a while since I posted another installment of the Things I’d Tell my 20-Year Old Self Series, so I thought what better way to get back into the groove than with a post from one of my favorite people on the Internet? Along with writing one of my favorite blogs, Akirah Robinson is a break-up coach and brave hearts enthusiast. What does that mean? Having been in an abusive relationship for 4 years, Akirah is now passionate about self-love and helping other women pursue healthy relationships. She believes we all have brave hearts.


I really could have used Akirah’s words and wisdom when I was going through my own abusive relationship when I was in my early 20’s, so it seemed fitting that she write the next Things I Would Tell My 20-Year Old Self post. Also, as you can see from the photo below she’s just all around lovely 🙂


(As I write this piece, I keep experiencing slight heart palpitations. I can’t stop thinking about the fact that I was 20 years old almost ten years ago. Hopefully I’ll be able to get through this.)

When I remember what it felt like to be 20, I can’t help but smile. Life was so simple back then and yet, I was so miserable. I had no real reason to be miserable, but I was. I mean, at that point I hadn’t yet kissed a boy or gone out on many dates. I couldn’t stop thinking about the fifteen pounds I “needed” to lose. It seemed like life would never work out for me.
So I smile. Because that discontent has morphed into extreme gratitude for the life I’m creating right now. I’ve come a long way, baby. Knowing what I know now, here’s what I’d tell 20-year old Akirah:

Yes. One day, you WILL kiss a boy. So calm down! It’s going to happen. In about one year, in fact. And while you’ll feel a little silly for being such a late bloomer, one day you’ll be glad boys didn’t distract you too much during high school and college. (In a few years when a show called “16 and Pregnant” debuts on MTV, you’ll be really glad.)

Take some time to learn the warning signs of partner abuse. Because honestly, you don’t really know them. And partner abuse is so much more than “my boyfriend hits me.” You’ll experience some crappy things during your first serious relationship and throughout much of it, you’ll be in denial about what’s really going on. Don’t fret though; this experience will teach you more than anything else has in your whole life. Even so, learn the warning signs. Then, tell your friends to learn them too.

Stop being a bitch about your love for Jesus. Seriously. People avoid religious fanatics for a reason, my friend. One day, you’re going to have to accept that people make mistakes. Let them. Then love them. And listen! Because no amount of preaching is going to convince your friends to live the life you think they should live. So just stop.

Your marriage isn’t going to save you. Yep, 20-year old Akirah. You get married someday. To a wonderful man, I might add. But this relationship will not save you, even though in the back of your mind, you kind of hope it will. In fact, in many ways it will stress you out. When you realize all those rainbows and butterflies were only a part of the story, you will struggle. So try really hard to not cling tightly to your expectations of marriage. Instead, work on yourself. Because your self-worth is not dependent upon your relationship status. And other people can’t save you.

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Things I Would Tell My 20-Year Old Self #13 – Tara

From trusting your intuition to surviving Fashion Week, “Life Lessons” have definitely been a theme in my life and on this blog lately. So, I thought this was the perfect time to just go with the flow and post another instalment of my Things I Would Tell My 20-Year Old Self series.


Today I have Tara of Magnolia Thoughts doing the honours. Tara is yet another one of the fantastic people I met at Bloggers in Sin City last year. Tara is fiesty and sassy and one of my favourite Sourherners 🙂 She’s also a fantastic writer and storyteller. I know I say this about all the posts from this series, but this is truly one of my favourite ones yet. Although I’ve met Tara in person and we shared some pretty amusing stories over brunch & a plate of crawfish, I feel like I know her better after reading this post, and I kind of just want to reach out and give her a big hug. I hope you enjoy her story as much as I did! Take it away Tara…

Whew. From where I sit now, self, 20 was quite awhile ago. I am almost 32, and there’s been what feels like a lifetime and a half of insanity in the intervening decade-plus. Let’s you and I have a sit-down. Have some sweet tea and kick back. I’ve got a little hindsight for you.

You are about to rush into something. SLOW DOWN.

20 was a big year for us. 2001 was an important year for everyone. In September of 2001, a whole lot of things changed very quickly in your life. And 9/11 will be more than a national tragedy for you. You won’t forget Peter Jennings simply muttering, “Oh my God,” as you watched that plane hit on live television. You won’t forget the shock, the panic, the frenzied rush to throw your stuff in the car and take off with your roommate across the Commonwealth of Virginia to your boyfriend’s fraternity house in the mountains. The sheer emptiness of the roads, contrasted with the gorgeous late-summer day, will resonate with you forever. But you will remember most of all walking into the house and seeing a vase of white roses, and hearing your friends say to you, “Did you hear about [friend]? How about [another friend’s dad]?” Gone in the Trade Center; gone in the Pentagon. 9/11 isn’t just a national tragedy. It’s the day your friend died in a national tragedy.

You, your friends, and your boyfriend will all grieve together. You’ll be at one of maybe 20 college football games played in the country the Saturday after. No one really knows what else to do, so they’re playing football. You will sing the National Anthem with this crowd, and you will cry. You’ll all wear black armbands for your friend, and drink cheap vodka, and spend a lot of time in confused silence. Your friend’s fiancee will come, too. She’ll drink and cry more than the rest of you. No one will know what to say to her. You’re all 20. You’re kind of useless in the face of large human tragedy. And that Saturday night, you and your boyfriend will agree to marry each other.

Dear girl: stop right there. Do not do this. You will be warned in other ways, too, by the people who know you best. Your daddy, when you call him the next day in your giddy tragedy-drunk joy, will say, “Don’t you want to shack up first?” You’ll think he’s joking. He is not joking. Your oldest friends will be happy for you in that weird way you’re happy for someone you think just might be doing something insane. You kind of are. And your insanity will be validated by all the tragedy-drunk 20-year-olds around you. When you announce your engagement, one of the frat-bros will pick you up in a huge bear hug, swinging you around and bellowing, “Thank God! GOOD NEWS!” And that’s really why you did this, self. You were desperately in need of some good news, some comfort, some ray of light to break through the grief-crazy. You wanted happiness so that the beautiful Virginia fall could be somehow justified when the world seemed to be crashing all around you.

You don’t have to marry him. You’re not really in your right mind right now. And ten years later, when you divorce him acrimoniously, you’ll realize that you both suffered because you made this snap decision. You don’t need a wedding ring to feel safe again. Pause. Breathe. STOP.

Send that letter.

You’re a tough kid, self. You’ve been that way for a long time. You learned it from your parents. You come from survivor’s stock. Except right now, “survivor” would be the LAST word you would ever use to describe your mother. She is unraveling before your very eyes right now. You understand what is happening intellectually. She’s sick. She’s major-bipolar. She’s relapsed on a couple of the addictions she’d gotten under control when you were a little girl and you made friends with other recovering alcoholics after AA potluck “eatin’ meetin’s.” You understand the reasons why this is happening.

Doesn’t make it any easier to deal with, I know. Calling repeatedly, with no answer on the other end for days, weeks on end; rambling, tearful messages on your answering machine; having to call the sheriff in her town to make sure she’s still alive – it’s more than you feel like you should have to handle. And on a certain level, you’re right. It is not your job to be the last tether holding your own mother to reality. And though you’ve done your best, you have finally said to yourself, you know, I just can’t right now. So you stop calling. And you don’t visit. You build the sad but necessary psychic space that you need to make room for yourself to grow.

This is not the wrong choice. There isn’t a “wrong” choice, really. And you’ll spend your twenties in a sporadic, tentative written chain of communication with your mother. But as she gets sicker, you’ll let the trail go cold. When you go to law school when you turn 26, you’ll mean to send that change of address, but you won’t. You’ll get to it eventually.

In 2008, the Super Bowl will coincide with Joe Cain Day, the most Mobilian of Mobile Mardi Gras observances. You, being a Mobilian, love Joe Cain Day. So you’ll think it odd that, after the parade and the festivities, along with that AMAZING end to the game, your husband’s phone is ringing. But it is, and when he answers, the time to send that letter is up. You will fly to Florida. You will take a boat with your daddy and his brother. Your daddy will tell you a story of your mother at age 13, and how she spent her mission trip will at once stir your pride in the woman who bore you and stab straight through your heart at how it ended. You will go to a memorial service at the group home where her life ended, and you will hear her friends give a eulogy that makes you realize that you really did not know her at the end at all.

Kid, send the letter. This one matters. When you’re crying at Thanksgiving dinner because you finally got that damn recipe for Mornay sauce right, but you can’t share that with the woman who handwrote the cookbook you use every fourth Thursday in November, you’ll think about that letter, and how it just never got sent.

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