To Date Or Not To Date? Please Answer My Questions

Written by Dee

Dating is so awkward. Dating is so uncomfortable. Dating is such a mystery to me.

And, as frustrating as it is, “dating” has been a huge part of my life lately (if you can call cross-country phone calls, meals that feel like interviews, or meeting boys for drinks and making out “dating”). It’s been an absolutely comedy of errors. Laughable, really.

I’ve just about reached my wit’s end.

Additionally, I’ve got the stereotypical single-girl gripe: It seems like everywhere I turn, there are couples. Happy ones, miserable ones, old ones, new ones, married ones, engaged ones, and gay ones. And here I am, stuck between longing to find my other half and being perfectly happy in my independent lifestyle.

Sometimes I can’t imagine being in a relationship and other times I’m downright lonely.

Frankly, I’m losing the energy to win the dating game. I’ve been playing the game hard for a year and I’m ready for a breather. I’m no good at it, I don’t understand the rules, and, most importantly, I’ve got other games to focus on winning. Bench me.

Because I’m beginning to blame my judgment.

Sadly, I’ve found myself staying in unhealthy relationships for far too long (years, even) because the thought of attending social functions, going to family holidays, answering the questions, dodging the judgment, explaining to everyone why it didn’t work out, and (cringe) dating again seemed exhausting, you know?

My philosophy of dating is to just fart right away. – Jenny McCarthy

I’ve got a bad taste in my mouth from kissing all these frogs. I’m beginning to become sarcastic, cyncical, and sassy towards the whole process.

I’ve dated the jock, the grad student, the frat guy, the neighbor, the musician, the nerd, the artist, the military guy, the childhood friend, the bartender, my dog’s vet, the pizza guy, and my friend’s ex. If you’re looking for Mr. Wrong, I can give you his number. From the guy who told me to “shut up” right before he asked to stay the night, to the guy that wore a flashlight attached to his head, and the guy who brought over the bag out of a box of wine to the guy who nonchalantly mentioned that he might be gay, I can see why it’s all entertaining, really. I’ve had some knee-slapping, unbelievable dating experiences. But, recently I’ve been asking myself, what is the point of enduring it all? To entertain my friends with my escapades? The occasional and short-lived ego boost that a meaningless hook-up offers? The off chance that I’ll find myself in a relationship that might work?

What is the point of blowing through these not-right-for-me gentlemen at a rapid rate? How is it serving me? Is it all just an effort to find “my other half?” One day, will it just “click” with someone? Am I putting in my time and is the pain of dating the only way to “Mr. Right?” And, can “self-love” be enough?

So many questions, and it seems the only way to find answers is to keep trying men on for size. Whatever the case, if I can find the motivation to keep playing the field, I’ve got to incorporate some sort of dating technique and practice habits that will make the game less brutal.

Stop crushing on anyone that a face: I’m like an effing wild animal in heat sometimes. If I’m out with friends and a single guy enters the scene, I pretty much start foaming at the mouth. I probably submit some terrifying frequency that alerts them to my desperation. He’s got a heartbeat? GREAT! So what if he’s a convict? I bet he’s really good at doing laundry. He’s five feet tall? I’ve always thought jockeys were cute. He can’t read? At least he’s not a pretentious lit junkie. You name the flaw, I can name the benefit it could offer and convince myself he is worth my time because who’s perfect, right? Wrong. Too often, my hormones hijack my ability to reason.

Refrain from taking interest in men for the simple reason that they are interested in me: Admittedly, I’ve got a bad habit of finding the good in any guy that takes an interest in me. At heart, I’m a people-pleaser. And I know that it takes some real guts to ask a girl out. But, even when my instincts are screaming at me that there is no connection with him, nor will there ever be, no matter how kind, smart, tall, or alive he is, I talk myself into it. By the end of the night, I’ve usually had too much wine, convinced myself that he has nice…ears or something, then I kiss him and all of a sudden he wants to go on another date and I confuse myself into thinking he could work as a husband. Yes, it would be nice to have a boyfriend. It’s also nice not having a boyfriend that I find to be just okay.

Decide what I am actually looking for: When it comes to narrowing the field, I don’t have a clue what I actually want in a partner. Defining them by their occupation, lifestyle, or look has always tripped me up in the past. It should be more about how he makes me feel. If he comes along and give me that feeling, great. If he doesn’t, I’ve still got my dignity and identity. And vibrator.

Everything I buy is vintage and smells funny. Maybe that’s why I don’t have a boyfriend. – Lucy Liu


Do I want to find a cutie with a beard and a passion for music, dogs, and me? Duh. Would I love to have someone to drink wine with, plan adventures with, and snuggle with on Friday nights? Sure. Do I think about “true love” and am I a hopeless romantic? Yup. If someone comes along and sweeps me off of my feet, would I be open to it? Absolutely. What will be good for me now, though, is working on the ability to weed out the jokes from the real deal. And, when I want a nice meal, I’ll start dating again.

As usual, thinking about this leaves me with more questions than answers. So, tribe, help a sister out. What’s your dating advice? What are your non-negotiables in a romantic partner? Did he appear when you stopped looking? How did you know when you’d found “the one?” Should I feel guilty for being happy to be single but also desiring the companionship of a boyfriend? Is it all worth it, or do you think “cat lady” would suit me? And please, share horror stories galore.

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