How To Make It Through The First Three Dates

As a relationship therapist, it’s not unusual for me to help my clients set up and optimize their online dating profiles. 

I do it when I feel they’ve done enough of the deep work to attract and be attracted to different kinds of partners — the ones they want — as opposed to repeating old patterns. 

And because a similar thing happened twice this week involving online dating, I felt it might be a sign that I need to put this lesson on blast, so here you go:

There’s a difference between being vulnerable early on in the dating process, and being so transparent about your budding feelings that you come across as too intense, desperate, or so into the person that you turn them off. 

Dating is different from being in a relationship, and so it requires a different set of skills and strategy. 

In dating, vulnerability [the act of sharing one’s personal story or feelings with another] is earned slowly over time. It is given in teaspoons. Not cups.

Small doses are necessary throughout the dating process so that the person you’re dating knows you’re into them, but when it’s given in great detail, too early on, it will have the opposite effect as what’s intended.

Here’s my list of Do’s and Don’ts for the first 3 dates:


  • Keep communication consistent.
  • Match their response time when you’re talking.
  • Dial up your confidence, which is always attractive. 
  • Keep texts brief so there’s stuff to talk about in person.
  • Be playful and flirt. 


  • Tell them how often you think about them. Or how you changed travel plans to accommodate a date with them. Or that you have to stop yourself from texting them every hour on the hour because they’re all you think about.  
  • Be long-winded over text, otherwise you’ll accidentally wade into a topic that’s too complicated to discuss properly in writing or say something that could be misunderstood.
  • Ask for reassurance. Trust what they say and do. If they say they’re OK with something, go with that. 
  • Self-flagellate if you make a mistake. Own it, apologize, then move on. Confidence is sexy.  
  • Engage in such serious topics that they can’t tell you’re fun — or worse — think you’re oddly intense. 


When you’re online dating, the goal is to book the first date. 

When you’re dating irl, the goal is to keep them intrigued so they’ll want the next date.