I'm Ready to Start Dating. Now What?

I went on dates with 22 people 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.

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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.

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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? It might sound obvi­ous, but cheat­ing means dif­fer­ent things to dif­fer­ent peo­ple. What would or wouldn't you be upset about your part­ner doing with oth­er people?
• 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.

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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.

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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.

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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.

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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.

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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 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!

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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.