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    Home » The Singles Chronicles

    How Single Women Celebrate Valentine's Day #TheSinglesChronicles

    Published: Jan 10, 2019 · Modified: Nov 20, 2019 by Jennifer · This post may contain affiliate links · Leave a Comment

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    Once upon a time, I was a kid who absolutely loved Valentines Day! My parents always made a really huge deal out of Valentine's Day for us kids (at least, that's how it seems 30+ years later). They'd take us to dinner, or to an establishment like Chuck E Cheese, and we'd have an amazing time. All of the goodies at the school parties! The exchanging of Valentine's Day cards - it was so much fun! As I got older and began liking boys, the romantic aspect of Valentine's Day became more obvious, and I would sometimes get a trinket from a boy I liked. Our high school also made a big deal out of this holiday, and certain clubs would sell $1 carnations, to be delivered to the person of your choice, in class. In front of everyone. It was a VERY BIG DEAL. I still have one of those flowers that my girlfriend sent me (I'd sent her one too), because neither of us even had a crush at the time. See, I've known How Single Women Celebrate Valentine's Day from the ripe old age of about 14...

    How Single Women Celebrate Valentine's Day

    It's changed a lot over the years. My very first Valentine's Day with a boyfriend - he was actually my fiance and high school sweetheart. He bought me a Singer sewing machine and we went to dinner at Chili's. Yes, he bought me a sewing machine...I know what you're thinking. AN APPLIANCE at 17? The thing is...I loved sewing. I used to alter all of my own clothes because I was so short, and sewing machines are expensive as hell for teenagers! It was a great present. I still have that sewing machine. 

    Want to Read More about my life as a single woman?

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    My next Valentine's Day with a romantic partner was actually my ex-husband, and we weren't even technically dating at the time, but it was the first time we'd kiss. I guess you could say that the rest is history?

    Valentine's Day changes as we get older. We have kids, we have responsibilities. We don't want to deal with crowded restaurants, bad service, overpriced menus etc. My-ex husband always bought me flowers on two days a year: Valentine's Day and my Birthday. Clearly, those were my favorite days! When we split up in 2015, I was scared. I hadn't spent ANY holiday alone, least of all Valentine's Day, in over a decade. So I did what any sane woman with money in the bank would do...I took Angeline to NYC (we let her boyfriend tag along).

    How Single Women Celebrate Valentine's Day

    It wasn't the first time I'd taken Angeline to NYC, but it was her first time with her boyfriend, and as they were both over 18, I allowed them to run amok, seeing all the sights, doing all of the touristy things. I kept trying to get her to come hang with my friend and I, but the only time we spent together was when I took the kids to the Empire State Building.

    2-Day Travel Itinerary for NYC Visitors

    Truth is, the friend I was staying with in NYC had plans and left for the day. I had two tentative dates lined up for that day, and they both flaked on me...so I spent the majority of the day alone, sitting in the park, taking a walk, eating Shake Shack...and doing a lot of self reflection. I ended the evening at the bar across the street, where the bartender gave the women - all 4 of us - a single rose and a Hot Toddy (it was a very cold February in 2016). He wasn't the only man to give me flowers that weekend, but that story isn't really relative anymore. I wrote about saying goodbye to that guy here - although it took us almost a year to finally break ties, and I am not especially proud of that.

    All in all, it wasn't a bad day. It didn't turn me into one of those I HATE VALENTINE'S DAY women.

    How Single Women Celebrate Valentine's Day

    In 2017, I actually had an impromptu, surprise lunch date with a guy I was casually seeing. Neither of us really thought much about it being Valentine's Day; he just happened to be in the area and asked if I wanted to meet for lunch. It was really nice. My friends tried to read WAY too much into the situation, but I knew him - he just didn't want to eat Chipotle alone. Ha!

    How Single Women Celebrate Valentine's Day

    That evening, my friend and I decided on Galentine's Day, as neither of us were really seeing anyone, and we were both kinda relatively single. She and her husband split the year after Chris and I did. SO we decided to spend it together at our favorite bar - which provided FREE CANDY.

    How Single Women Celebrate Valentine's Day

    We had a great time, as we always do, and when that guy from earlier texted, we decided to invite him to join us. It was his first Valentine's Day since his separation and we didn't want him to be alone. He did join us, and we got a free ride home out of it (saved us money on Uber since he only stayed for one beer).

    I have to include this ridiculous Snapchat story from that evening, because we do one every year and it's definitely become a tradition!

    The next year, I was 100% single again, and she was not, yet somehow THAT morning, I met a guy on Tinder, and neither of us realized it was Valentine's Day. He asked to meet after work for a beer and I agreed. When I told my friend, she freaked - YOU MADE A FIRST DATE FOR VALENTINE'S DAY?

    Yep. That is the level of my stupidity when it comes to dating. I don't even think about these things!

    How Single Women Celebrate Valentine's Day

    As it turned out, he was actually married and totally lied to me about being separated and I swear, nothing happened between us. I could feel right away that he was lying and sneaking around, and I couldn't trust him as far as I could throw him...he was a 6'2" cop, so you can imagine that wouldn't be very far.

    However, Bri showed up to save the day, and while she had a date with her steady guy that night, we had a round of beers together and the day didn't suck after all.

    How Single Women Celebrate Valentine's Day

    So, all of this to say...I am not even remotely dating anyone right now. Remember the Great Year End Purge? No one made it through. NOT A SINGLE MAN. I did try to keep Macklemore around, but he's stopped texting again, so I think he showed himself to the door.

    So what am I going to do for Valentine's Day this year? I have two besties in Miami, and one is married and other might as well be. I can't go asking either of them to ignore their significant others and hang out with me - that's not super romantic. So here's what I plan to do on Valentine's Day...

    But don't worry, I still plan on buying myself flowers and making a fat ass steak with mashed potatoes. The way to my heart is through my stomach too!

    If you're looking for an alternative to sitting at a bar with your other single friends this Valentine's Day, check out this post I recently published 20 Ways to Celebrate Valentine's Day - it's all happy, family stuff and has some really good recipes!

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    About Jennifer

    Jennifer, AKA "The Rebel Chick," is a 40-something Gen Xer who strives to help her readers live their best lives possible with easy recipes, travel inspiration and lifestyle tips!

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    Hi, I'm Jennifer! I'm a Miami native and I love sharing easy dinner recipes, baking recipes, travel ideas and general Miami Lifestyle fun! Follow along for inspiration on how to make the most of your life!

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