Friday, February 14, 2014

Tipsy's Embarassing Valentine's Day Challenge Steps 1-9 (2014)


So this year, after a particularly bad week preceding Valentine’s day and after a lot of pleading from one of my besties I decided to do this ridiculous single ladies challenge. Lets just say it was a very interesting expirence… eye opening even.

At first the challenges seemed simple enough, embarrassing but simple and I can totally handle making a fool of myself to strangers. Don’t do this alone kiddies its super stranger danger-y but with friends its soooo worth it. But before I knew it the challenges morphed and I was stuck staring at my phone and the number of 3 of my exes. What’s a girl to do when faced with possible life altering conversations about past failed relationships…. You freak of course and try to find any alternative to said conversations, and that my lovelies is where great friends come in. A friend has the ability to make you question your sanity, tell you to cheat or even to shoulder on, pull up your big girl panties, and just rip the damn Band-Aid off. I chose the latter and the 15 minutes it took for a response left me with stubs for nails and a severe case of anxiety.

So lets back peddle a bit and I can explain this better. This challenge consists of 15 steps. As many of you guessed, they are completed by either submitting a screenshot or video clip. I got to do a mixture of the two ^_^.

Step 1: Alright Ladies! Today is the day of love, Aphrodite, Lady Venus didn’t see fit to bestow you with a suitable suitor so its time to show the world that your IDGAF attitude. Hit up the nearest clothing store and pick up the tackiest pink outfit you can put together. Don’t send us a picture, don’t send us a video just read on for step 2.

Step 2: Wear it in public. Duh! Like you little vixens didn’t see that coming

Step 3: Talk to a complete stranger, no laughing no jokes! They totes can’t know that this is part of a challenge, Be serious ladies. Send a picture….

Now for the safety of my self-respect and the identity of this individual, I will not subject you to Tacky Tipsy’s morning in Walmart but I will include a picture of the dreaded articles of clothing. Let’s just say that clothing was promptly returned once the steps were completed.

Meet my tacky outfit, add knee length pink socks and my mortification is complete.



Step 4: Buy yourself something nice, something sexy
Step 5: Buy yourself something sweet or alcoholic your gonna need it. My advice…. Buy both.

I bought myself a new lip-gloss. I know, I know soooo risqué (note the sarcasm my loves) but I was a tad strapped for cash and I really like the shade of coral. It did nice things for my complexion. Now for step 5, I bought myself Raspberry Ghirardelli Chocolate Squares… yum. But I wish I had the foresight to buy myself some wine cause boy oh boy did I need it after I finished Step 6.

After a particularly bad week, I had a completely unnecessary woe is me cry fest with cookies while I asked a friend of mine what the hell was wrong with me that I couldn’t seem to keep a relationship working… It was depressing and totally not me but hey we all have craptastic days. Anyway this friend of mine had this brilliant idea that I should contact some of my exes and find out from them. I mean I know why I wasn’t happy with the relationship and why it ended on my part but I never once thought to ask why they felt it was over or what compelled them to do whatever it was that made me angry or hurt.

The truth is, I didn’t want to know. Who in their right mind, with any amount of sanity intact would consciously ask these questions that had the potential to warp your whole view on your past relationships and maybe just maybe make you the bad guy. Obviously, not me. So I completely disregarded that advice, did the straight up girl thing and went on with my pity party… I’m not a pretty crier, I should have taken this friend’s advice. Had I taken their advice I might have been prepared for step 6.

Step 6: Contact 3 of your most recent exes. Find out why your relationship fizzled. Send us the screen shot. We are trusting you with this ladies so no cheating ;)

Now if you’ll just refer to the beginning of this post that life altering conversation… yep multiply that by 3 and you have my dilemma. I legit sat there for 40 minutes weighing the pros and cons of dropping out of this challenge. Go through with it and possible have my heart shattered or back out and disappoint the bestie. What a conundrum… But you all know me too well and I could never knowingly disappoint my friend. So I followed through. For the sake of the identity of the guys involved we will refer to them as Scumbag and Douche Bags and Mr. Charm your pants off. (I'm so nice, aren't I)

My group message consisted of “Alright boys. Before you get any ideas this message is solely for the purpose of a Singles Challenge. It is not an attempt to converse with you further than the response to this question and I will in no way be opening that door again. So lets not attempt to revisit the past.



In your opinion… Why did our relationship end. Please lets be mature about this, lets not go with the simple answer or you dumped me or vice versa. Thanks! And Happy Valentine’s Day”


The first to respond and shatter my perfectly built mental walls was Mr. Charm your pants off. His message stated the following: "It didn't work out because you were too good. Tiff, your beautiful, you were the perfect girlfriend and that shit scared the fuck outta me. You gave me space, you didn't care if I looked at girls cause you were confident in yourself. You seemed to real to be true and men, at least me, we can handle perfection well."

See what I mean about Charm your Pants off. If he wasn’t already snagged and part of a completely perfect couple I might have had a complete case of lack of judgment and wrote back, set up a meet and well you get the gist of it lol. Luckily for me, he is, she’s a doll and I would never… no could never stoop that low.


Promptly following that was Scumbag with. “Shit happens Tiff. We were young and I wasn’t down for commitment when there were so many hot chicks around. What are you doing tonight?”


I literally sat there dumbstruck. Did this boy not know how to read and ‘what the hell’ was I thinking when I started to date this clown in the first place. I'll just file that under the 'Lack of Judgement' I spoke of earlier. So that was 2 down and 1 to go… the clock ticked and I got more antsy by the second, taking to skype to talk to a fab friend. Finally after what seemed like hours, but in reality was probably only 20 minutes I got the final response.

“Hey Tiff. Happy Valentine ’s Day. How have you been? Well to answer your question, I was really insecure in our relationship. I think I loved you too much and I get it that you had some issues to sort through but you didn’t make me feel any more secure in our relationship. It was a lack of judgment on my part and I shouldn’t have cheated on you. I don’t think I ever said sorry. If I didn’t then I’m sorry. You were too good to me, you were like a best friend and I really miss that. I miss having you there. I was tempted and I gave in. You were worth fighting for, your walls were worth the struggle cause that girl I caught glimpses of was the most amazing girl I ever met. Even at your worst you were beautiful and caring and I fucked that all up.”

Now the only reason this gentleman was dubbed Douche Bag is because, well he’s a cheat and he made me cry not only at the end of the relationship but reading that. It’s safe to say I loved this guy to bits and I was absolutely devastated. But then I got the text with the next challenge and this one was by far the best and most hilarious of all the challenges.

Step 7: Laundry and Lace…. Just because you're home with a pile of dirty clothes and no sizzling hot date, that doesn't mean you have to look like a hag. Sexify yourself ladies, throw on your most flattering nightie and clean away. Mix a drink and strike a pose. I guarantee you’ll feel super sexy.

Now this was an absolute blast. I was scared, shitless might I add, I live with 2 males and walking around in my nightie is a big no no but the spectacular friend on Skype talked me through it. So with a new attitude and spunk I don’t normally possess… I locked my door threw on my nightie, blasted some tunes and danced around to make myself feel better. My dance of choice was the Risky Business dance sans the glasses and socks and done to the tune “I Hate Myself for Loving You” by the ridiculously talented Joan Jett. It was priceless and fun and truth be told I did feel sexy once my room was clean. My snap shot included me in a black and teal laced nightie posing provocatively with my leg wrapped around a broom and a drink in my hand lol. It was something that definitely will never see the light of day but it made me laugh and better yet made my friends laugh. It instilled a confidence I didn’t know I could possess. The FedEx guy may or may not have gotten an eyeful when he surprised me at my door O_o

Step 8: Belt it out. Pick your favorite Disney love song and belt it out. Ladies we need proof. Send us a video clip at least 20s long.

As an ode to my heartbroken ways and my absolute love for Disney I chose. “I won’t say I’m in Love” sung by Megara in Hercules. There isn’t much else to say about this challenge <3

Step 9: Alright Ladies, wind down, relax, and pretty yourself up. Wait for further instructions as you hit up the town for steps 10-15. Remember that something sexy ladies… nows the time to bust that out.

...So now I kinda wish I picked something sexier than a measly tube of lipgloss…

La Dolce Vie and all that jazzy.


So here’s the dress I chose for the evening…



Tune in tomorrow for my rundown on the final 5 step ;)

Thanks for stopping by,