How to Date: Essential Tips for Building Strong Connections

By Selina Nguyen

In the age of social media, influencers, and ChatGPT, there is so much repackaged and recycled advice, and random, yet specific, dating tips.

Headlines such as “wait until date 3 to have sex”, or incredibly vague cliches like “just play it cool,” and the painfully long lists of green flags, red flags and “icks” that seem to just keep growing are rampant on our social media feeds. 

The struggle with dating, loneliness, and finding connection, is nothing new, and it’s possibly more difficult than ever.

The sheer volume of advice and hot takes that we’re faced with each day on our screens can feel completely overwhelming, and this can make it rather difficult for us to discern what is our authentic self and what is cultural programming when trying to navigate the world of dating.

What comes through in a lot of conversations during client sessions is that Cancel Culture and Disposability Culture has also leaked into how we connect, date, and have sex.

Being Imperfect

These terms “cancel culture” and “disposability culture” refer to the idea, and very common experience, that if we make one mistake, we’ll be cancelled, replaced or ghosted.

There’s an emphasis on showing up perfectly all the time, and as a result, dating can become more of an exercise in mental gymnastics than a felt and embodied experience.

So often I hear variations of the same questions: “What if I say the wrong thing?”, “What if I embarrass myself or make them feel uncomfortable?”, “How do I know when I’m supposed to kiss them?”, and the age old question, “Why can’t I just relax?”

Hear me when I say that you’re not alone in this.

Folks across all ages, genders, neurotypes and abilities, are struggling to make deeper and more meaningful connections in many ways, including platonic, romantic and sexual.

From research, we know that loneliness can have negative impacts on our overall physical health equivalent to smoking fifteen cigarettes a day. But what do we do when we’ve never been taught the relationship skills in meeting new people, building intimacy, or what goes into creating and sustaining deep relationships?

As the kind of therapist who loves structure and a good plan, I recommend starting with creating a dating plan for yourself.

Building a Dating Plan

I build on this idea from Dean Spade’s recent book, Love in a F*cked Up World, where they suggest a dating plan to help us stay grounded in our intentions, values, desires, and in connection with others.

Creating your dating plan requires you to reflect on the moments where you get stuck in your head. Where in the dating process do you lose yourself in hormones and New Relationship Energy (NRE)? How you can keep yourself accountable?

This can include boundaries with yourself. For example:

  • I will take three slow breaths when I catch myself overthinking

  • I will have regular check-ins with friends

  • I will make sure that I keep up with my solo time

  • I will follow and stick to safer sex protocols

  • I won’t wait by the phone for their text

  • I won’t sacrifice time with friends to see them

  • I won’t obsessively check their social media profile

  • I won’t drink more than (insert number) drinks on a date

The focus of these examples isn’t “how do I be more attractive or sexy?”

Rather, it’s “how do I stay connected to myself throughout this fluid process? When I inevitably disconnect, how do I come back?”  

This reframe towards staying connected to ourselves means that we’re creating more opportunities for our authentic selves to show up on dates.

When we’re feeling anxious or overwhelmed, there is little space for our creative, funny and sexy parts of ourselves to show up.

You don’t need to be more attractive or sexy. You already are! It’s about being present with who you are.

Often we look towards the Cosmopolitan articles, social media influencers and ChatGPT first because we want quick and easy answers, but we also want security and reassurance that we’re doing a good job. 

However, this outsourcing of reassurance to online dating gurus and influencers can mean that we never get to build self-awareness, self-trust, or what I refer to as our internal compass.

As a result, we also don’t get to learn the relational skills that go into building intimate relationships, because we’re focused on following these made-up rules and scripts about waiting until the third or fourth date, playing hard to get, and monitoring who texts first. 

Your dating plan can also include some of these skills that you want to practice more. For example:

  • I want to practice asking deeper or different questions

  • I want to practice directly telling people what I like about them

  • I want to practice asking for touch that I want

  • I want to practice offering touch 

  • I want to practice coming up with new date ideas

With each date, you can pick one or two that you want to set as your intention and focus on practicing, and notice the difference in how it feels for you.

Dating As We Are

This intention setting shifts the question from “Am I following the right script?” to “Am I present and connected with you?” “How am I feeling in this experience?”

When we cling to the script-following and don’t develop our own internal compass, it can make it rather difficult to discern if we actually like someone or if we like the idea of them - f this person has the attributes of being a good partner or if it’s just the raging hormones.

For many folks, breaking away from the social script to write our own can feel risky and vulnerable, and such is the work of intimacy, but this is the price we pay in order to be seen and loved just as we are, not for how well we play the role. 

Building intimacy and trust doesn’t require the absence of this fear. Rather, it asks us to tell our fear that it is welcome here, and that’s what your dating magazines and ChatGPT won’t tell you. 


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