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How to Have a Successful First Date: How to Survive the Awkwardness

Updated on April 23, 2012
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Stuart has spent three years trying to convince his boyfriend he is not hiding books under their bed and they are certainly not multiplying.


So, my lonely single friend, you want to try your hand at dating, again? You, like SO many others, are surrounded by coupled friends - watched as they reaped the benefits of duality - and have finally given into your petty jealous and crippling loneliness. You have purged your kitchen cabinets of tubs of frosting, countless bags of chips and enough CoolWhip to keep all the children in the neighbourhood happily rotund for, at least, one solid year. You even went out and bought celery to snack on when you are not going for brisk walks around the block or to flirt with the twenty-three year old barista at your local Starbucks while ordering a skinny iced, two pump vanilla, soy mocchiato. You are obviously committed to find Mr(s). Right.

There is nothing in your life more important than landing your perfect (wo)man, so I have dedicated myself to helping you land your perfect person to show-up your annoyingly committed friends.

the costume change: dressing for the occasion

If you are, truly, serious about landing yourself someone, before you've stumbled into middle-age therefore rendering yourself invisible and chance of relationship obsolete, you've begun dressing in outfits which say, "hello, i'm available but not desperate and very fashionable but not vain because I just threw this on when I rolled out of bed". Since you're now dressing to impress any attractive person you come in contact with, you can no longer be seen in public wearing sweatpants - throw them out; ritualistically burn them in your backyard; or donate them but get rid of them. Your family and friends are more willing to help you - setting you up on blind dates with their co-workers, friends or doctors children - when you stop showing up to functions looking like you walked off the set of Kids.

You, lonely one, are no longer dressing for yourself, instead you're dressing for the companion you'd like to attract most, for example; for women, white bikinis seem to attract millionaires (you'd be the final trophy on display in his home - exciting); and, for men, board shorts and those washboard abs, starvation uncovered, seem to attract the bored trophy wife looking for a twenty-something plaything (tip: try accessorizing with a pool skimmer or lawn mower whenever they're readily available).

Your clothing is the first to go when you're entering the dating world, they've been tarnished by single'dom and have no place in your new life - they should all be donated to charity. The new you should be fashionable and always, no matter what, look better than anyone you're with; yes, I'm asking you to practice peacocking - it's not just for the cast of Jersey Shore anymore.

where to find my perfect companion: hai, you got options

Okay, so you've just finished purging your closets and drawers of that dirty singles wardrobe you amassed and have begun the hunt for your soulmate. There is nothing more embarrassing than having to ask one of your married friends to accompany you to a singles bar, it doesn't seem to matter how unattractive they are, you'll still be forced to watch them be hit on by everyone in the bar while you sit alone. You could go alone but that would be truly pathetic and, knowing your luck, they'd find your body three days later behind the bar shoved, head first, into a dumpster.

No. You cannot just meet people and expect it to work out, you need to be realistic, this is NOT the movies. The modern day, relationship seeking, individual has one, truly, viable option, yes, the internet - it's like speed dating but with personality summaries. You needn't suffer through the depressing cocktail hour, schmoozing some arrogant investment banker or sassy legal assistant, when you can quickly scroll through their profiles - favourite the ones you want to revisit later and send messages to the ones who catch your eye.

And with those provocative, black and white, semi-nude shots you uploaded to your profile it won't be long until you're the toast of eharmony or When they ask to meet - do it - choose the most public place you can think of; whether it be a Starbucks or Blimpie's make sure you look fantastic, he/she could be the next Bayside Butcher, so make sure you leave a beautiful body (or, at least, nice pieces).

someone say conversation? some topics to avoid when wooing the love of your life

We all know you're the most interesting person in the room - your life rivals Harry Potter in content - but it's always nice to tone down your, obvious, awesomeness for your date; let him or her talk about themselves, no matter how boring listening can be. I, once, went on a date with a guy who told me he was uncircumcised to explain the extra time he spent in the bar bathroom, this is the kind of information one does not need over first date drinks. I would also avoid talking about long-term commitments, keeping the conversation light on words, such as; marriage, pregnancy, wedding and birth.

Did you love your ex? Did you think s/he was the one you were suppose to spend the rest of your life with? Did s/he cheat or gamble away large sums of your money? These are all wonderful conversation starters for your therapist, but, unfortunately for you, in your pursuit of free psychiatric care, it's a date killer - then you'll be left with a whole new set of issues to discuss on your next date, oop, I mean doctors appointment.

Really, my friend, this first date is your only chance to impress this person and make them believe they're unable to live without you - unable. to. live. without. you. Just because everyone, in your life, thinks you are loveable and perfect doesn't mean you'll win this person over, teddy bears are loveable, and you don't see anyone dating them - I mean, honestly, none of your fawning friends has ever asked you out.

So, instead of talking about your hopes, dreams and aspirations, let them talk about themselves and make sure to adopt all their interests during the meal or over coffee. Do you like laughing at bad jokes? Learn to and make it convincing - practice on a friend before the date.

With commercials, magazine ads and the mass media telling us we'd be better off with someone rather than alone, what's a single person in the city to do? How can someone debate the fact a single person is 34% more likely to die younger than their married off counterparts - even death is telling you to find someone - and still not feel the pressure to couple up. It would almost seem that being single in the current society has become taboo, and a little sad - suddenly, after a certain age, you've become the sad lonely friend more concerned with work than finding a loving relationship.

So, my single compadres, get out there! Time is ticking away on your life, literally. If I've learned anything from reading dating advice books, articles on finding love and anything Elle publishes on relationships is that it's never about being yourself, when it comes to finding someone, it's about becoming the person you think they would want to love.

Happy dating and don't forget to settle!


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      Kellzenful 5 years ago

      Damn this will be hard :/