July 29, 2014

To All The Single Ladies: 10 Tips for Dating in Your 30s.


Early last winter I made a big decision. A brave one. A scary one. A necessary one.

I decided to write the ending to a chapter of my life, the beginning of the end, as it were. I wanted to start the next (possibly painful) adventure in the little journey of my life I like to call “my current reality.”

As much as I didn’t want to go there again (or, let’s be honest, to don something other than yoga pants), it was time.

Having spent a good year getting reacquainted with myself and my charming set of idiosyncrasies, I recognized the occasion calling for me to stop avoiding male attention and to start practicing the art of social bullshitting again.

Yep. That’s right. It was time to start dating.

Oh boy. Bring on the awkwardness.


Dating in your 30s is hard. I have created a life so full of fun and friends and work and kids and personal fulfillment that finding time for the average guy was uh, well, not so reasonable—thus the ensuing “search” for Joe Squared commenced.

Did I master the art of courtship? Um, no. I did, however, learn a lot about myself and my priorities, about the dating process, about other people and that I have an entire closet full of clothes but nothing to wear. Serious problems, you know?

In any case, I collected some (good?) advice and stories, and in honor of my sisters and brothers fighting the good fight, here are my notes from the trenches. Read carefully. Plan wisely. Share strategically. Laugh generously.

The CTFD (Calm the F*** Down) Guide to Dating.

1. Own your own shit

You are who you are and that’s the end of the story sister. If you feel compelled to present yourself as something other than who you truly are, to have interests that you don’t really have, to know things you don’t really know then you are in trouble, my dear. That facade will only hold up for so long. Be willing to grow and learn and try new things—but label them clearly as such. Don’t be a poser. Know what kind of eggs you like.

2. Don’t be such a drama queen

Seriously. Chill. Out. Don’t take anything personally, nothing others do is because of you. Slow your roll, dial it back about 1,000 notches and stop reading into every teeny tiny little everything. Just as you respond to things based on what’s going on in your life and in your head, so do other people. It’s actually not all about you. Shit. Little “good news, bad news” delivery here. Yikes.

3. Don’t make assumptions

First impressions are important, whether they are virtual or in person. However, misrepresentations happen, and often, especially via electronic communication. Sadly, there is no sarcasm font, and emoticons will only get you so far in nonverbal response. Additionally, credentials are just paper—a job, a degree, or a “pedigree,” so to speak, is only one small part of a person, it is not who they are. A degree does not equate intelligence, nor does the lack of one indicate the opposite. Gather some facts before drawing conclusions. However…

4. Be skeptical, but learn to listen (to your gut)

Unless you: a) have endless time on your hands, b) like spending it running in circuitous motion, or, more likely, c) enjoy learning lessons the hard way, listen to your intuition. Really. If something tells you it’s not right, it’s probably not. Know the difference between simply being uneasy because you are getting out of your comfort zone and what is legitimately no bueno para ti. Don’t spend your time trying to make something work that you know isn’t going to; things that are meant to be aren’t usually that complicated (well, unless you make them that way, in which case, please re-read #2).

5. Always do (be) your best.

This shouldn’t be difficult, it should be easy to be the best version of yourself around people with whom you spend time. If it’s not, then it’s time to move on to something better. Relationships are about bringing out the best in each other, not the worst, and not the person someone else wants you to be. Just you, the best you, whoever that is today.

6. Look where you’re going

Leave your past in the past. Seriously. There is a time and place for viewing the skeletons in your closet and unpacking your baggage. First, second, even third dates are not it. Your past has shaped who you are, it has shifted your paradigm and your perspective, but it is neither your present nor your future. Stop inviting the Ghost of Christmas Past to dinner with you, nobody likes a third wheel.

7. Be quiet already and stop oversharing

Ask don’t tell, listen more than you talk, and stop sharing your entire life story in the first hour. Ditto with explaining yourself—knock it off. People earn the privilege of hearing your personal information and story by earning your trust; save it for the right people. Be authentic, humble and genuine. Your actions speak louder than your words, and uh, your selfies. Photo overshares to new acquaintances, by the way, come off as a marketing ploy. Translation: you’re trying too hard and it’s not hot. Like, not at all.

8. Trust the universe

Everything we do prepares us for something else, for better and for worse. A bad date helps us to enjoy a good one, a good relationship gets us ready for a great one, a painful or arduous experience tests our composure, flexibility and resilience. Be grateful for the opportunities provided, in whatever form they come. That being said, be ready to see them; stay open and choose your concessions carefully. There is a difference between a compromise and settling, a big one. If it comes let it come, if it stays let it stay, if it goes, well, let it go.

9. Don’t go chasing waterfalls

The right person will come at the right time and for the right reasons. Being overly responsive or attentive is a bad plan; the idea of “the chase” isn’t meant to be you cyberstalking and checking in every hour. Stop. Now. No. Just no. This means that if your messaging pattern goes from phone blowing up to you staring at it, nonstop, checking to make sure it’s working, you are pretty much done there, sweetheart. If he responds intermittently to you, then yeah, you’re not the only girl in his contact list. Let that one go. Taken from the mouths of our wise elders, “Don’t make someone a priority who treats you like an option.”

10. Plan your escape route carefully

Seriously. I have “rescued” a friend from a bad date, recently, and while wearing my “Spiritual Gangster” tank top. It was half awesome, half hilarious. I personally have zero problem calling it when I see it (politely of course), but it’s taken me some solid practice to learn the art of the graceful exit. Some things to remember: 1) take a cab if you can, use a ride sharing app if you really want to do it right, so you can “call” them slyly from under the table and then suddenly “voila!” it’s time to go, no awkward waiting around, 2) meet for coffee or a drink, not dinner, and 3) don’t stand someone up, that’s just bad form (and bad karma). Be honest with what’s going on. Don’t be an ass but keep it real (translation, do not have a friend call you with a fake emergency. I promise you that is not going to end well).

BONUS: For those of you looking for an Independent Love suited to a New Generation.
Relephant Reads:

How to Avoid Self-Sabotage in Relationships  

> Soul F***ing: a How-To 


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Editor: Travis May

Photo: Wiki Commons

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