back to Relationships

A longer version of this piece was originally published in 2012 in Tara’s blog, Redefining Single. Here, she takes us back to the days before emojis and OkCupid were tossed around in general conversation, and reminds us of that original confusing dating tool: the humble text message.

My closest friends are married with children, married and thinking about children, engaged, or in serious relationships with pending engagements (this was my former category, until it wasn’t). As I transition into singledom again, my sister Anna has been my tour guide, leading me through all sorts of culture shock and answering my ridiculous questions.

Some examples of my phone calls (many at ungodly hours of the night):

Me: “It’s been 45 minutes and he has not texted back. What is the appropriate emoticon to get this conversation going again?”

Anna: “Tara, do not . . . under any circumstances . . . text him again. I want you to hang up with me, go put your phone in the car, and leave it there.”

Me, ignoring her very sane advice: “You didn’t answer my question…which emoticon is the most appropriate?”

Anna: “I’m coming over.”

Texting has been one of the biggest adjustments to the Land of Single for me. Yes, I texted before, but never to have a conversation. Only to confirm a day/time/location or answer a yes-or-no question. In this new form of existence, texting with a boy is highly stressful and has rules that I was completely unaware of prior to my life being catapulted into uncharted territory.

Whether you want to admit it or not, you’ve probably had many of the same questions that Anna has so graciously answered for me. So to save you all some time, I’ve compiled a texting cheat sheet.

The all-important blob size: I am notoriously long-winded, which has not served me well in throwing “text game” at boys. You need to be cognizant of the size of your text blob: if your blob is five lines long, and his is only one, you’ve f’ed up. Unfortunately, my introduction to texting is within the age of the iPhone, which means the boy can see the “…” while you are typing. This poses another completely different challenge, as you don’t want a lingering “…” because you want to be effortlessly funny and charming. Meanwhile, my “…” is on his damn screen for an hour while I rework my novel (being excruciatingly aware of my blob size) and then my “…” disappears as I backspace my novel and reappears when I settle on an emoticon in lieu of what I actually wanted to say. I inevitably end up looking like the longest and most indecisive smiley face typer of all time. (While we’re on the note, emoticons are the ABSOLUTE WORST. Can’t someone think of a better way to convey sassiness than a winky face?)

The wait-to-respond: This is hard-to-get strategy at its finest. When discussing this with my friends, the takeaway was that you want to appear as if “something suddenly came up” and you can only get back to the text when your highly important life slows down. This, my friends, is not my reality. If there is any delay in my response, it’s because I’m trying to come up with a succinct and charming comeback that does not create a too-large blob (see above). If I do manage to miss a text, it’s probably because I am doing something SUPER URGENT like cleaning an air filter in sweatpants.

Text? What text?: So, my first post-breakup date is looming. And I’m going to let you in on a secret: this is actually the first real date that I have ever been on. I’ve been on plenty of already-in-a-relationship dates with boys (well, two boys) I was already dating, but never like this. And this date is with the cute boy involved in most of the above texting, and I am outrageously nervous for several reasons. On top of my normal (okay, above-normal) anxiety, I have been told by everyone and their mother that I am not allowed to directly reference the hours of texting we’ve done. So wait a second: I’ve been smiley face-ing my ass off, agonizing over my blob size and frequency, and being delightfully witty and charming . . . and I have to pretend it didn’t happen?!? I guess it would be awkward if I was like, “So remember that time you texted me that you liked me and I texted you back a winky face?” But still, to utterly ignore it has happened is beyond me. To be honest, though, the hives will probably be so distracting he won’t know what I’m saying. (Silver lining.)

Texting Hangovers: Texting is way more fun while drinking (most things are, arguably). I am charming, hilarious, and have waited the perfect amount of time between texts . . . and then I wake up. And so begins the Texting Hangover. Unfortunately, chugging water and taking Excedrin cannot cure this unique and complicated condition. The hangover begins with the re-read. I have (out loud) asked myself, “Really, Drunk Tara? Last night was the time you chose to disclose that you have a metal allergy and your ring gives you a finger rash?? Cute. Really cute.” You see, all of your calculated and strategic texting can unravel after just a few beers. (To add eternal insult to injury, in the land of texting, your finger rash story is immortalized in print and revisited as soon as he does his own “re-read” the next day.) The second stage is waiting on the first sober text, post-drunken rambling texts. The waiting is difficult, but is compounded by your actual hangover and the vulnerability you feel after disclosing personal information (see: finger rash, above). So you are on the couch, wrapped in a blanket, trying to pretend not to care, and when the phone does finally chime, it generally looks a little like this: “Soooo . . . how are you feeling today? :)” Damn beers. Damn hangover. Damn finger rash. The only thing that you can do is insert a winky face and start rebuilding your texting credibility. 

Here is my proposed solution: all iPhones should be equipped with a Breathalyzer app. If you blow anything over stone-cold sober, your texting privileges are restricted to emoticons only. 

In any case, I’m off to this date – despite the finger rash, the poorly composed text blobs, and the lack of restraint in my replies. I must be doing something right. Wish me luck! 😉


Tara Sampson started out, as most do, with the intention using her Master’s degree in her career. She was initially successful in this effort working as a Child Life Specialist at the MUSC Children’s Hospital in Charleston, SC. After a few years, she left the gorgeous coastal town to return to Gainesville, FL where she serendipitously fell in love with the fitness industry while working in management with Gainesville Health & Fitness, and left the tangible application of her Master’s degree in the past. After four years in Gainesville, it was time to switch it up. Tara rented out her home, sold her furniture and moved a carload of her belongings to Washington, DC for a fresh start. This start began in the basement of her cousin’s home with his cat named Stinky, but quickly turned into her own apartment and a position as General Manager for VIDA Fitness. Through her time in the health care and fitness industries, Tara developed a passion for pushing boundaries in health and redefining proactive and preventative health care. Most recently Tara was offered a chance to join One Medical Group, an amazing start-up literally transforming the delivery of health care. Tara is now the Regional VP: Enterprise for One Medical in DC, and uses her diverse background in health care spectrum to integrate the One Medical vision into the DC community. Oh yeah…she also has this blog highlighting her generalized awkwardness specifically in relation to dating: Her sister has endearingly renamed the blog, “Tara Will Be Single Forever Due To Oversharing On The Internet.” read more about