On The Pros and Cons of Dating a Teacher



Currently, I am a single woman out in the world just trying to make it on my own. I take my own self on dates. My most regular good morning and good night texts come from my mom. The last man to tell me he loved me and was proud of me was my dad. I don’t have to shave my legs on a regular basis. Most of the compliments I receive regarding my appearance are from children at school (MISS JOHNSON, I LOVE YOUR TUTU TODAY – a real five year old compliment I received on a skirt I was wearing). Every night I return home to Olivia Johnson, party of one. For now, I am 100% okay with this. As selfish as it may sound, I like being the focus of my own life at this point in time.  However, someday I am sure this will all change. This is what concerns me. Teachers are their own type of people. They come with a specific set of challenges for anyone who may choose to be in their life. I pray that my future partner is currently garnering the strength and patience necessary for dating a teacher, because, trust me, he will need it.


Pros: I love school supplies. There is nothing that gets me going quite like a BRAND NEW SET OF SHARPIES (getting the chills just typing this). I get a thrill out of organizing pens and markers. A fresh stack of Post-It notes brings me legitimate joy. Each year, when stores set out everything for back to school shopping, it is a thousand excited children and also me. WOW! LOOK AT THESE SWEET FOLDERS COVERED IN PUPPIES?! I THINK I NEED A NEW GLITTER PENCIL POUCH! The Kate Spade line of office supplies was the greatest thing that could have ever happened in this cruel and cold world. I was given a miniature laminator several weeks ago and legitimately burst into tears (cannot make this stuff up).  If you EVER need any type of supply, odds are I have it (and most likely in my purse). I can complete your school and work projects like a pro. I am never without a pen or pencil. I can use my myriad of fancy note cards and pens to make your shopping lists and fill out your planner. I am so super organized. IT WILL BE GREAT.

Cons: I love school supplies. You will see my tubs and tubs filled with crayons and stickers and begin to wonder if I am insane. Each time I go to reach for a mint in my purse and instead pull out a miniature stapler, you will be embarrassed by me. You will be both amazed and disturbed by my NEED for fun eraser toppers for pencils. THE KIDS NEED THESE, IT IS LIFE OR DEATH! Single paychecks will vanish in the blink of an eye. “Won’t your school pay for this stuff?” you may be wondering. LOL, MY FRIEND. LOL.


Pros: I am obsessive. I will always know exactly what is going on in your life. Work schedule? I’ll have it memorized within a week. Birthday? I’m on it. Birthday of a family member or friend? I’ve got you. Big event? I’ll know every detail of what is going on. Your friends’ likes and dislikes? Covered. I’m obsessive, which means I’m also a planner. Date night? I’ll whip us up an itinerary immediately. I’m great with dates and times. Does your mom have book club next week at your house and she is feeling anxious? I WILL TOTALLY REMEMBER AND THEN ASK YOU ABOUT IT.

Cons: I am obsessive. I have actually woken up in a panic at 3 am with these exact thoughts: “IF WE HAVE SNACK BEFORE GYM, THEN I DON’T THINK WE WILL ALSO HAVE ENOUGH TIME FOR RECESS”. How terrifying, right? I am unable to let things go. I will worry and worry and worry until I exhaust myself. You will most likely get tired of hearing about my concerns about every little thing that seems completely unnecessary. “JUST DROP IT, LIV,” you will beg as I bring up something we have already discussed way too much.


Pros: I will regale you for hours on end with stories of all that has happened at school that day. I can easily turn a small anecdote into a half hour long tale complete with voices, actions, and facials. You will feel as though you know each child personally due to my alarming number of funny moments I am eager to share. You will be SO ENTERTAINED! This quality makes me great at small talk. I can talk for HOURS. You will never feel awkward or as though you have to scramble to make conversation. On our first date you will most likely not even have to say a word. How lucky for you!

Cons: I will regale you for hours on end with stories of all that has happened at school that day. You will grow weary of hearing EVERY SINGLE LITTLE THING that occurred during my eight hours with students. “YOU WILL NEVER BELIEVE WHAT HAPPENED…” will grow to be your least favorite sentence starter. When you are trying to enjoy a movie and I lean over and whisper “oh my goodness I forget to tell you what _____ said today!” you will cringe and give an inward sigh of annoyance.


Pros: I love children. There is nothing I want more than a family of my own someday – your mom will be so excited. You will never have to worry about me getting along with the kids in your life. My experiences with children have made me patient (usually), affectionate, and empathetic. These traits will serve our relationship well. I am great at hugs, and I can for sure tie your shoes.

Cons: I love children. When we go on dates, I will not once be able to focus on you. I will be too busy making faces at the baby across the room or chatting with the four year old sitting next to us. Romance? Totally dead. At any social gathering that we go to of your family’s I will most likely immediately gravitate towards the kids’ table in order to socialize with “my people”. I can talk Lego Ninjago, Doc McStuffins, and Junie B. Jones for hours on end. SEE YOU LATER.


Pros: Sometimes I act like a child. If you are ever in need of a juice box or granola bar, odds are I have one in my purse. This is not a joke. AT ALL TIMES I HAVE A SNACK ON MY PERSON. You will never be “hangry” while in my presence. Like a child, I am incredibly affectionate. Public hugs, kisses, and hand holding do not frighten or concern me in the slightest. I’ll always be there when you need comfort! While dating me, it’ll also be totally okay to indulge in the childlike activities you once enjoyed. Coloring? LOVE IT, I OWN AN ADULT COLORING BOOK. Disney movies? PERFECT, I KNOW THEM ALL. Petting zoos? Count me in. Ice skating? WONDERFUL. You never have to worry about your own interests and passions being embarrassing, because mine are far worse.

Cons: Sometimes I act like a child. When we are out in public with your friends and I won’t stop quoting my favorite movies (MOVE IT, CREEPY – Robin Hood) you might become alarmed and annoyed. “Sorry about her,” you’ll apologize as I am pretending to be a sneaky Kronk from the Emperor’s New Groove (this one is for you, Lauren and Maggie). You will be frustrated by the fact that, at the age of 23, I still use words like “tummy” and “bottom”. Odds are, at some point, my inability to watch scary movies or do anything remotely frightening will be bothersome.

In conclusion…

Hopefully, for someone, the pros will outweigh the cons. Teachers are interesting people. Kudos to you, my future person. I can only hope you will be prepared for me.



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