Man- Day Post: Why I Don’t Miss Dating as a Teenager

In Man-day by Jensguy16 Comments

Welcome to Man-day with Jensguy!

I have reached that awkward time in my life where I am starting to see the pictures of girls going to prom posted on Facebook by the mothers of the girls that I myself went to prom with.  Ahh, Technology!  My children are blessedly younger than that so I have a few more years to personally deal with that myself.  (With good behavior my 12 year old daughter might be able to attend a prom when she is 21.)

Seeing these pictures has taken me back to my teenage dating years that I tried to repress, and made me consider some things that might not have been common knowledge to you women:

1.  Prom Pictures.  How many people out there have kept copies of their prom pictures?  Unless you ended up marrying the guy in them I would suspect precious few.  You need to know that unless his mother got a hold of them first, most guys dropped those things in the garbage can right after he gave you a copy, if you wanted them.  Here is the real thing about those pictures, they amounted to an “I don’t dance” tax.  So unless you were all:




chances are that you didn’t have enough moves to fill up a couple of hours on the dance floor, let alone being able to bust them in a rented tux.  So in order to delay, delay, and delay, you visited the punch bowl a few dozen times, and waited in the interminable line for prom pictures.  That alone could kill half the time you were supposed to be on the dance floor.  And how badly did we want to avoid dancing?  This bad:









Incidentally in the 6 years that I have now been attending elementary school daddy-daughter dances, this phenomenon is still in full effect.  A lot of daddies are still afraid of the dance floor and even today continue to wait with their daughters in line for pictures.

2.  The Phone Call.  If any of you ladies were ever called on the phone by a poor boy asking for a date, I hope you were nice to him.  Honestly, I have handled a number of challenges in my professional life and have been placed in a number of uncomfortable positions, perhaps none of them quite as excruciating as dialing that last digit of a telephone number preparing to ask a girl on a date.

In retrospect, much of the fear and pain was unnecessary, but for somebody as unfamiliar with life, things, and especially girls, it was certainly life or death.  Consider: If she answers the phone, you are going to have to make up small talk before you actually ask her out.  You can’t just blurt out, “Hi, this is Jimmy! Will you go out with me?”  (Well, except that roommate I had in college that often employed this approach.)  You need to identify yourself and then move smoothly to “Sooooo, what are you doin’. . . .”

What if she says no?  Because it isn’t likely she is going to say “Get lost, creep!”  She is more than likely going to say that she has something else going on.  Should you try again at a later date, or assume that she wants noting to do with you.  Teenage boys are going with option “B” almost every time, unless he is a stalker, or just really confident.  Chances are he was a stalker.

What if she says “yes?”  Now I have to plan a date.  That is a whole different set of worries and pitfalls.  If I feel the need for moral support, I will need to go on a group date.  That will entail me waiting for my friends to sit through the Hell that I just endured.  What if they give up and I’m left to fend for myself?  That is why it was important never to be the first to ask, which is probably why a lot of girls aren’t getting asked out in high school. It is possible that things are different post-Carly Rae Jepsen, however. . .

3.  Budget Woes.  It’s really hard to impress a date on a high school student budget.  You can have dinner OR a movie if you are lucky.  Nowadays, I suppose couples split the cost, but I was, and still am a gentlemen, so unless it was Sadie Hawkins (whoever that was) the guy was paying.  Fortunately I grew up rural so I had a lot of options not open to city folk.  We did night hiking, cow tipping, ice blocking on golf courses and a bunch of other things that will likely get kids arrested today.  Here’s ice blocking for those wondering what it is:

Also, some boys also had to resort to driving the family station wagon when going on a date, which was a step better than needing their father to drive said station wagon.  In this, I was lucky as I had my own set of wheels, which looked a lot like this:

except with a lot more Bondo to cover the rusted out parts.  It was all ready for the paint job I was never able to afford.  It would have been sweet, and went perfectly with the stereo system that was easily worth more than the car.  Yeah, it was pretty much a Love Machine that cost so much in gas that I could barely get to school and back.

So, yes, dating was hard and didn’t resemble at all most of the teen drama shows on TV.  I don’t know if there will be a lot of advice that I can give my son that will help him ease through those years, other than to Cowboy Up and Soldier On.  I did stick with it and became proficient enough that I was able to finally catch Jennifer, so I suppose it wasn’t all bad.  I never have taken her ice blocking, however.  You all should nominate that for her next Pinterest challenge.


  1. Bwahahahahahahaha! YES! Now that you mention it, dating as a teen was no easy road! I guess we didn’t have any better experiences to compare to, so it all evened out…ish?? Still, how brave are boys for having the nerve to EVER ask a girl to the prom (especially in this day and age that it’s a big production where they have to not only ask, but do something AMAZING while doing it. YIKES!) You are so right, teen dating *really* doesn’t resemble anything that you see on TV! –Lisa
    The Dose of Reality recently posted…Would You Rather: Plan It All Or Be Surprised?My Profile

    1. I always thought that girls had the advantage because, unless it was a very strange situation, like a blind date, the boy had to have above average interest in a girl in order to ask her out. Of course that allowed us to never have to go on a date with someone that we didn’t want to, which I can also see as an advantage. I supplemented my prom fund by helping other boys ask out girls in a “cute” way. It was no different from having than enlisting the aid of “deal on flowers” guy. Sometimes it took a village.

  2. “Honestly, I have handled a number of challenges in my professional life and have been placed in a number of uncomfortable positions, perhaps none of them quite as excruciating as dialing that last digit of a telephone number preparing to ask a girl on a date.” – Awww! Girls (and many women) do NOT realize this! We’re SORRY! :( ;)
    Valerie recently posted…Know Your Exposure (Reducing Wireless Radiation during Pregnancy)My Profile

    1. Of course, in retrospect, if a girl actually gives you her number, than this SHOULD have been easier. It wasn’t. So if you ever gave a boy your number and he didn’t call, he still might have been into you, he was just terrified of phone small chat, which many of us struggle with to this day.

    1. Jennifer tells me that there is a high probability that you went ice blocking as a teenager based on where you live. The best part really isn’t the ice blocking itself, but the sneaking into a golf course at night so you can use the well manicured slopes that work the best for the least amount of friction. Enjoying yourself while remaining just a step ahead of the security guard with flashlights is a rush. Of course you didn’t need to tell your date that the security guard was your best friend’s older brother that you had already paid off with a value meal from Wendy’s. That would have ruined the moment. . .

      It would be fun to see Jennifer scale the fence and evade capture while ice blocking, however. We’d have to do it with night vision to do it correctly.

  3. HAHA! Ah, I don’t miss it. I didn’t really date as a teen but I dated as a pre-teen (just..why?) and as a college student and as a young adult.
    It was all somewhat amazing and somewhat disastrous.
    I watched a lot of 80’s movies as a kid and I just thought dating in high school would be like that. I guess I’ll never know.
    Tamara recently posted…A Face In The Crowd.My Profile

    1. Well except The Breakfast Club, life ALWAYS resembles the Breakfast Club. And pre teen dating, isn’t that when you are “going with” someone and don’t actually go anywhere?

  4. ugh dating in general no matter the age is hard. I only ever dated two people one before my hubbie and then my husband and that was enough for me so I just thought I would keep the second one and now 10 years and 3 kids later I’m still happy with the decision.
    Becka recently posted…Jumper Dress with Pocket – Sew and Show PostMy Profile

    1. Count yourself fortunate. I have to admit though that dating as long as I did finally paid off in the end as it took that long to find Jennifer.

    1. Actually, Florida and Arizona is where it works the best due to our natural lack of snow. It’s a warm weather substitute for sledding. All you need is a block of ice from the local gas station, a hill with grass on it, and a towel to keep your butt from freezing. You need at least 2 for racing purposes.
      jensguy recently posted…Man- Day Post: Why I Don’t Miss Dating as a TeenagerMy Profile

  5. I’m so glad I didn’t date in high school–I think I escaped some awkward memories! I’ve seen my husband’s prom photos and I can’t help but laugh at how funny they look…
    Rachel G recently posted…Avoid Student Loan Debt!My Profile

    1. Oh yes, they are terrible. My husband found some of my old ones and showed the children, note not his, and the children almost died from laughter. We really should advise people to not take them or if they do burn them before their posterity can get wind of them…….
      Jen recently posted…Host Your Own Old Fashioned Summer Watermelon BustMy Profile

Leave a Comment