Dating do’s and don’ts.

In the past year, I have embarked on a slow but steady dating journey.  Because, you know, having my entire life upended professionally and personally didn’t provide me with enough upheaval, change, and emotional battering.  Nope, I needed to make sure I was juggling every major ball I could: job, home, and love.

In spite of all the said upheaval, change, and emotional battering, in the last 12 months, the energy, time, and effort I’ve put into dating has, actually, satisfied and surprised and bolstered me a great deal.  It has proven a welcome outlet.  I have been able to say to myself, “Well, even if the job isn’t quite what I want, I need a paycheck, and I promised myself I’d give it a year.  And even if my home situation isn’t ideal, I have committed to staying put at my sister’s until reaching a certain date and a certain amount in my bank account. But…love?  Dating? Meeting new men?  Now THAT I can control.  THAT I can feel good about.  THAT I can call wholly my own.”

Oh, how time changes us…

Rewind two years, and I never, ever would have imagined myself writing that, considering I spent the majority of my twenties so tightly closed to meeting men and to trying to date.  The romantic in me just wanted to bump into some tall, lanky, farmer-meets-musician-meets-successful/established-professional-meets-kind-hearted-man-who-writes-well.  Yeah.  Steep.  And I was unrelenting.  And I didn’t do or change a single thing despite not running into these kind of guys left and right.  Wasn’t love supposed to fall into my lap “when I least expected it”?!

No.  Why did it take me all of my twenties to get that?

Regardless, I did get it.  I do get it.  Which is why I have finally taken the reins on romance and reeled it in and reminded it that I am, actually, in charge of my fate and my love life, thank you very much.

And so here I am to share with you—and, selfishly, to document for my future self—what I have learned about dating in the last year.  It is a modest list.  It includes lessons both painful and hysterical.

It is a reflection of my firm belief that dating is like anything else in life:

Maintain a good sense of humor, a realistic optimism, and a steel-strong belief in your self.

Do remember this.

Do accept offers to be set up…so long as you confirm the other person knows exactly what’s going on, too.  Transparency is key, my friends.

Don’t hate on your married/in-a-committed-relationship friends who gush about how “awesome!” and “exciting!” dating is.  (Anyone who has been single for any amount of time and has chosen to make a conscientious and concentrated effort to date knows it is anything but “awesome!” and “exciting!”  It’s expensive, exhausting, emotionally draining, and seemingly endless.)  Do tell these friends they might not 100 percent know what they’re talking about but thank them for their enthusiasm and encouragement all the same.

Do offer to pay.  Actually, always offer to pay or at least split the bill or cover the tip or, if nothing else, feed the meter.  It’s just good manners.

Don’t pretend. If you’re not into the person, you’re not into the person.  And you certainly aren’t doing him/her or yourself any favors by acting otherwise. Life is short; move on.

Do clarify what you want and what you need…as soon as you know you want and need it.  You can save yourself weeks of wondering, months of “exploring possibility,” a sharp moment or two of heartsick pain and hurt, with one, honest, mature, and direct question and conversation.

Don’t settle.  I know—how cliché.  But, really.  Don’t.  Love should never, ever feel mediocre or come with the explanation of “Well, okay. This works. We have a lot in common.  It’s easy.  I guess.  Why not?”  There are, I’m sure, 100 reasons why not.  Do be honest with yourself.

Do go for passion.  Whether that passion is physical or emotional or intellectual or conversational or some fantastic combination of any/all of the above.

Do suggest locations or activities you want to try.  Good excuse to finally check out that new restaurant or comedy club or art exhibit.

Don’t accept any offers to play “a little game” on the second date.  Hell, even on the first date.  The guy might be suggesting you play a round of cards…that have sex-themed questions on them.  And he might seriously want to play.  And think that’s perfectly appropriate…  (Yes, true story.  I lived to tell the tale.)

Do remember to laugh.  A lot.  At all of it.  The horribly written e-mails, the ridiculous pictures, the lame questions, the poor manners, the bad jokes, the pang at evening’s end when you realize, with a disappointed sigh, “Nope, not this one. Next?”  I mean this seriously and sincerely:  if it’s not funny, it quickly becomes tragic.

Do go with the flow.  Schedules shift; plans change; problems arise at work.  Stuff happens.  Roll with it.  (I recently went on a date where the power blew in the restaurant because of a massive fire downtown.  There he and I sat, in the near-dark candlelight, with no hope of the dinner we’d planned, and proceeded to still have a great time.)

Don’t over-book your calendar or double-book a night.  You are either going to leave one date earlier than you want to or arrive to another date later than you’d planned.  I have learned this lesson the hard way.

Do whatever it takes to feel good in your skin: flirt, wear lipstick, rock heels, don a new dress, get a blow-out, order a fancy drink, buy some new lingerie, squeeze in a yoga class, take advantage of a reason to look fabulously beautiful.

Don’t take the interview approach.  Do make sure you’re able to ask questions beyond, “Where are you from?  What do you like to do for fun?  What’s your five-year plan?”

Don’t question yourself or what you have to offer.  Do believe in your worth, your greatness, your intellect, your contribution.

Don’t listen to everyone else’s advice.  Listen to your own.

Do revel, thoroughly, in those early thrills of, “Ooo…I like you.”

Do practice kindness and compassion.  Dating is basically an exercise in presenting yourself, asking, “So. You interested?”, and then awaiting a verdict.  Rejection always stings.  Do keep this in mind when you’re delivering your ruling.

Don’t play games.  You’re an adult.  Behave accordingly.

Do take leaps, take risks, push yourself past your comfort zone.  Do not be afraid to fall.

Do stay open.  Do not—I repeat: do not—limit yourself.  How else can you learn?  How else are you surprised?  How else do you give someone (including yourself) an honest, fair chance?

That said, do have standards.

Do communicate.  Respectfully, honestly, and in a timely fashion.

Don’t give the “I really hope we can still be friends” speech.  No one likes to be on the receiving end of that line.

Do take a step back if you need to.  Do take time to reflect.  Do take time to heal.  Do lean on good friends and family.

Don’t take too long, though.  Don’t drag the past behind you like a child lugging a tattered, snot-covered lovey.  Don’t linger on the ones you’ve lost or the ones who left you behind.  Move on already.

Do make your own list of do’s and don’ts.

Because if I have learned anything this year, it is this:

I know I am an incredible woman who has an incredible amount to offer and who will be an incredible life partner, wife, and mother.  (Incredible!  Apologies—I just finished Extremely Loud and Incredibly Close.)  But, incredible aside, if I want something in this life, I do have to work hard for that something.

And, these days, that something is love.

Do believe in love.

Do believe, whole-heartedly, in finding it.

5 responses to “Dating do’s and don’ts.

  1. Wow! I love playing games. Like hearts, cribbage, etc. Not all games are tacky.

    The ironic thing is that I LOVE (yes, all caps) playing games. I have been known to carry a pack of cards with me in my purse. But…a sex-question game on a second date? That’s tacky.

  2. See – this is what they should be writing in all of those “women’s magazines”. This is real, honest, and the best damn list I’ve ever read to prepare anyone going into or going through the dating game. Beautiful.

    Oh, honey. Just wait until you hear the stories that are behind this list… Can’t wait to see you!

  3. “Don’t listen to everyone else’s advice. Listen to your own.”

    That is the truest thing I have read today.

    Glad it resonated. Thanks for reading!

  4. A Super Girl

    I’m imagining the card guy as saying “come over and we’ll play a little game..” in this super creepy, borderline pedophile voice. Please tell me that’s how it happened.

  5. This is a WONDERFUL list! You’ve clearly put a lot of thought into it and I’m going to refer any friend with dating woes to your corner of the blogsphere! But … I must disagree with one point. I didn’t meet Sweets until I was almost 33, which means I had over a decade of serious dating experiences until settling down. Dating absolutely was fun and exciting and any time I felt it was a chore, I stopped dating. I feel like so many people date to find the one. WRONG. Date because it’s a part of your life’s journey. Because on your life journey, you want to have fun, interact with interesting people, try new things, etc. Date because you want to share your life with others. Otherwise, that well-worn road known as life becomes merely transportation, not an adventure!

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