I’m Ready to Start Dating. Now What?

I'm Ready to Start Dating. Now What? 1

I went on dates with 22 men within 13 months between relationships. People get exhausted, just hearing that statistic.

While meet­ing peo­ple to date is often sim­ple, it’s not nec­es­sar­i­ly easy — I don’t want to min­i­mize the time and ener­gy it takes. It’s eas­i­er said than done to stay pos­i­tive but authen­tic when dating.

Take a breather. This post is a reminder that:
  • Intentionality is key in every­thing you do.
  • You’re not alone in your frus­tra­tions with dating.
  • Self-love comes down to what you want out of life.
  • You know your his­to­ry bet­ter than any­one else.

1 Keep your own needs in mind first and foremost.

Finding what you’re look­ing for — espe­cial­ly if it’s a life­time rela­tion­ship — may or may not hap­pen as fast as you’d like it to. Like me, you might go on dates with 22 peo­ple before set­tling down with some­one you real­ly fancy.

As such, it may be help­ful to have a game plan for dat­ing your­self:

  • What are your needs, wants, and desires?
  • How can you ful­fill them with or with­out a partner?
  • What oth­er peo­ple and resources can you reach out to?
  • How can you give that atten­tion to yourself?

It’s not pes­simism; it’s hav­ing your own back and tak­ing steps to make your­self hap­py, no mat­ter what happens.


2 Check your assumptions and calibrate your beliefs.

Everyone has a dif­fer­ent set of expe­ri­ences that shape their views on how dat­ing “should” be — what’s expect­ed in a rela­tion­ship, or what it means to be in one at all!

Where we often get in trou­ble is when we assume oth­ers think the same way we do. The more you can clar­i­fy your expec­ta­tions, the better-equipped you are to express your per­spec­tive and see your date’s or partner’s view.

If you still aren’t see­ing eye-to-eye about your yel­low, red, and orange flags, it’s bye-bye.

Consider the following potential causes of misunderstanding:
  • How open are you to being friends with a date? What’s your date’s stance on friend­ships with peo­ple of oth­er genders?
  • If it’s exclu­siv­i­ty you’re look­ing for, what does that mean to you?
  • How do you define “friends with ben­e­fits”? That could be any­where from a several-night stand to a full-on friend­ship with­out a monogamy escalator.

3 Remember that everyone has an exciting story to tell.

Some dates are just awful, but most peo­ple have sto­ries that you can learn from.

What tri­als and tribu­la­tions have they been through in their life? What child­hood mem­o­ries make them smile? What are they proud of? What do they wish they could tell their younger self?

Sample unfa­mil­iar facets of the human con­di­tion with them and expand your per­spec­tive, even if there’s no esca­la­tion after the date.


I'm Ready to Start Dating. Now What? 2

4 Keep it a sustainable system — whatever that means to you.

If dat­ing is exhaust­ing, it’s okay to take breaks or rethink your dat­ing strat­e­gy.

Some do bet­ter when mak­ing quick, gut-based deci­sions about whether they see a future with some­one after the first or sec­ond date. Others pre­fer to keep the con­nec­tion low-stakes at first so that they:

  • Give their date a chance to become attractive.
  • Don’t hype up or project on their dates too much.

The health­i­est thing to do is often strike a bal­ance between, “I’m striv­ing for what I want in the long run” and “It’s going to be what­ev­er it’s going to be.” Do what works authen­ti­cal­ly for you.


5 Have a support team — or at least a few wing-partners

On the flip side, self-love doesn’t mean that you have to exist in iso­la­tion or do every­thing 100% alone. Friends who offer alter­na­tive per­spec­tives and keep our blind spots (refer back to point #1) in check make life a lot easier!

That applies both when we’re stuck in our beliefs, and the oth­er end of the spec­trum: waver­ing and need­ing a reminder of what’s impor­tant to us.


6 Remember that the right person for you will offer plenty of flexibility.

If you’re cring­ing at a first date or an appar­ent “mis­take” or moment of dis­con­nect, that’s okay. It’s part of being human. It’s good to have some self-reflection and moti­va­tion to do bet­ter, as you know better.

However, if you’re the kind of per­son to self-flagellate under a micro­scope, take a step back and see the big­ger pic­ture. Intentional dat­ing isn’t about per­suad­ing peo­ple to like you or alter­ing every lit­tle thing about yourself.

Learn about your­self and the oth­er per­son. Find out whether you’re a good fit. If two peo­ple aren’t right for each oth­er, then not being togeth­er is the right out­come. It’s not nec­es­sar­i­ly about what you did wrong.

You can’t “make” peo­ple love you, but the right per­son for you, right now, will appre­ci­ate your quirks and what makes you, you. Stay authen­tic and true to yourself.


7 Reflect on what you’ve learned.

A spread­sheet or quick bul­let jour­nal of your dates can be a trea­sure trove of insight. Keep track of:

  • What went well
  • What didn’t go well
  • What you learned about compatibility
  • What you would do differently

I'm Ready to Start Dating. Now What? 3

I found that spreadsheeting my dates helped me:
  • Give myself cred­it for the things I did right
  • Appreciate the work I already have done
  • Re-affirm that there are plen­ty of good peo­ple out there
  • Recognize old pat­terns, both good and bad 
    • Turns out, my pat­terns weren’t what I thought they were!

8 Above all, trust yourself!

You know your needs, wants, desires, and his­to­ry bet­ter than any­one else. Before you take advice from some­one on the inter­net who’s nev­er met you, con­sid­er their bias­es and where they’re com­ing from.

(I’m aware of the irony, but here’s the thing: I don’t push a one-size-fits-all solu­tion to every­thing. I’m only pro­vid­ing the per­spec­tive of one per­son who’s been there and done that.)

Discard what feels dis­em­pow­er­ing, restrict­ing, or like absolute bull­shit. Take what res­onates with you, because it’s ulti­mate­ly you who will reap the rewards of your decisions.


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4 Responses

  1. Erica says:

    Thanks so much for this. I real­ly enjoyed #1; above all, tak­ing good care of your­self and ful­fill­ing your desires and needs with­out the NEED for a part­ner. It can be real­ly hard some­times! But it feels so grat­i­fy­ing, and whole to treat your­self with love, and kind­ness, and patience, and good (self) plea­sure too. I real­ly enjoyed this arti­cle a lot. I’ve also gone on many dates this year (iron­i­cal­ly dur­ing COVID, some of them masked and dis­tanced, some not), and am always fine tun­ing what I think is a com­pat­i­ble match. Letting go of expec­ta­tion is a real­ly awe­some part of the jour­ney, and a tough one. Thanks again!

  2. Prudence says:

    These are great tips! It’s way too easy to burn out when dating.

  3. D. Dyer says:

    As a human with spread­sheets for every­thing, a lit­tle sur­pris­ing I’ve nev­er con­sid­ered a dat­ing spread­sheet so thank you for the inspiration.

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