The Post Third Date Check-In
The importance of review and introspection after the third date.
So you’re coming off date three and thinking about what’s next.
The first date, with the inherent slight awkwardness, is done.
Date number two went well enough with its deeper learnings and vibe checks.
Now, with date three completed and some more understanding of this potential romantic interest, it is time to ask ourselves the hard hitting question of “is this something I want to seriously continue pursuing?”
Social Conditioning
The biggest obstacle to overcome is the social conditioning of the instant spark, love at first sight, and other overly dramatic tropes when it comes to romance.
We get this from movies, tv shows, books, and the handful of true instant love stories that sound so good we all want it for ourselves.
But we need to remind ourselves that the instant ignition is more a myth than a reality. If we look at the psychology of it, we’re more than likely feeling a pull because of physical attraction and some underlying attachment issues we haven’t yet corrected.
What to ask ourselves
If we can ground ourselves in curiosity, and set aside any distracting spark (or lack thereof), we can focus on these key questions that will help us understand how best to proceed:
Have I been enjoying their company? If you’ve made it to date three it hopefully means they are tolerable enough. But beyond being tolerable, have you been enjoying their presence? Is the conversation interesting? Are they playful? Is there good banter? Has the physical touch been at appropriate levels? Are they behaving well towards you and others around you?
Do I feel good about myself when around them? Is your authentic self able to come out? Do you feel seen, heard, understood? Do you feel safe? To a degree, this is an aspect of relationship we need to work on within ourselves. But after three dates, you should have some sort of read on whether the person across from you is creating a safe space. More importantly, are you able to show up as your authentic self and still be accepted?
Are our non date interactions positive? You’re probably texting, connecting on social media, or even calling each other between dates. How do you feel when you see their name pop up on your screen? Do you light up and smile a little bit? Or do you let out an exasperated sigh? Are they coming across as too needy or are they barely reaching out at all unless you make the first move? Be aware of your own behavior and anxieties around connection, but your answers to the above can be telling as to how you feel.
Is the thought of a fourth date appealing or even exciting? If not, then that is definitely something to consider. If meeting up with them again for a full fledged date feels like a chore, then that’s an important signal to pay attention to.
It is incredibly important to develop self awareness so you can answer the above as honestly and clearly as possible. Relationships get so tricky because of the emotional baggage each person brings into them. We often delude ourselves and ignore red flags, project our own insecurities, and can set unreasonably high and unfair expectations.
The ultimate question to ask ourselves is this:
Am I dating them because I actually like them, or because I don’t like being alone?
Physical Intimacy
It would be remiss of me not to bring up sexual intimacy because many people believe that some degree of action should have occurred by the third date.
I’m not here to advocate for or against and certainly not to judge.
What is important to note is that sex can sway opinions one way or another when it is this early in the courting. It could place a partner in the role of “situationship”, “friends with benefits”, or even worse being strung along emotionally so the physical benefits can be reaped. On the other side of things, it can supercharge infatuation and the feeling of connection leading to a rosy colored view of things.
That is why I will urge you proceed with caution and get a feel for the emotional maturity of the other person while keeping in mind your own.
Something I will recommend is that if you have any doubts when it comes to answering the above questions, it might be better to hold off until you’re clear on what you do or do not want to pursue.
The Next Step
The necessary questions and considerations have been listed.
We understand the need to self awareness and introspection, for looking beyond any initial physical attraction and spark.
I’m hoping up to this point, as well, that you’ve kept an open mind regarding “type”. If you ever find yourself saying something along the lines of “all the guys I meet..” or “all the girls I meet..”, the problem is you. Simple as that. Do the work on yourself, broaden your horizons. Basically, be a good person looking for good people.
Back to the main point, we’ve had the third date and asked ourselves all the questions.
Well? What are your answers?
If it isn’t a resounding “YES”, that’s ok. You’re not marrying the person. Remember what we talking about regarding the spark being a fiction? I don’t think its fair to expect it to ignite over three dates. So if you overall have a positive impression of the person, think they’re cute, and wouldn’t mind hanging out again, then do so.
I know I definitely find myself putting the cart in front of the horse because I don’t want to make mistakes and waste time. But quality time with another human being, even if they don’t turn out to be “the one” is never truly wasted. Everyone has something to teach us and connection is so precious.
If any of the answers to the listed questions were a definite no or even an “I’m not sure (anything less than “yeah”), then this ain’t the one.
The introspection is important to ensure you’ve been bringing your best self to the dates. But if the humor isn’t matching, there’s already an apparent mismatch in values, and you don’t feel safe and seen with them, cut your losses and end it.
PSA, when ending things, do not ghost. I repeat. DO. NOT. GHOST.
Be an adult. Send them a text (unless you run into them often enough to warrant an in person conversation) with something along the lines of:
“Hey [enter name], I’ve been thinking about us and, while I have really enjoyed spending time together and getting to know one another, I don’t feel a deeper connection developing. I do value the time we’ve spent together, but don’t think we’re the right fit for each other romantically. Thanks for the time together and wishing you the best of luck!”
You can add a line about wanting to stay connected and be friends but only if you are sincere about it.
You do not have to give specific reasons why beyond what I shared above.
Fun note, this is an actual text I sent recently to someone a few days after our third date. She was lovely, but there were just a few areas where I didn’t feel we were connecting and the conversations started feeling forced.
Be realistic. Be honest. Pay attention to your internal reactions.
Remember that dating is a journey, an experience, that is meant to leave us better off afterwards with fond memories and lessons learned (the learning may not always be the most fun part, but I digress).
I hope this helps you on your dating journey!


