Why Don’t My Relationships Go Beyond Three Dates?

More than just a few dates

By: Lincoln Giesel, LCSW

It can seem as though romantic fulfillment is getting more and more difficult to pursue in the era of dating apps, a broader dating pool overall, and an increasingly fast-paced culture.  In a city like Chicago, with potentially hundreds of thousands of hopeful singles in the area, it can be hard to feel as though you are consistently having positive dating experiences.

This post aims to address a few potential reasons why you may be perpetuating a cycle of casual dating and staying stuck in the earlier stages of relationship building.

You’re rushing the process

To gauge if your first three dates were “successful,” you must first determine how you truly feel on the dates.  Try and relax your attachment to treating dating like a game or an interview process.  Your short-term goal in dating is just to determine if you enjoy spending time with the person and would like to continue to get to know them.  If you notice yourself spiraling into anxious thoughts around your long-term prospects with this person, that may simply be a sign of your enthusiasm for them.

On the first handful of dates especially, it is helpful to reorient yourself to building intimacy in a more gradual and relaxed way.

You’re trying too hard

Perhaps that people-pleaser streak begins to take over and you make the dates about impressing the other person, rather than enjoying the present moment.  It is important to practice being at peace with the reality that not every person you date will want to dive into something serious with you, or vice-versa.

Related: Struggle with codependency? 

If you find yourself getting in your head about your likeability and worth (which is inherent), the antidote here is to be your authentic self.  While this is easier said than done, you can always harness yourself to your values, your desires in a relationship, and your true personality when you are feeling secure.  Imagine how you would behave if you were with a trusted friend, or if you were less threatened by the idea that this person may reject you (which happens to everyone and is a necessary part of the dating process).

You’re not trying hard enough

Think of the early stage of dates as an opportunity to put your best foot forward and consistently demonstrate your interest (if the interest is there).  This suggestion particularly applies to folks who have a more avoidant or distant dating style.

Dates are not a time to be too coy or set up indirect communication patterns early on.  Some of the advice we receive about dating when we are younger (i.e. play hard to get or keep it cool) do not necessarily apply to healthy adult relationships.  Someone who is a solid match for you will not be threatened by your showing an appropriate amount of enthusiasm in the earlier stages of dating.

Rather than waiting a few days for a text or being indifferent about date plans, try taking a more proactive and reciprocal approach.

You’re being too judgmental

We have all seen that notorious dating profile that has a list of narrow requirements right off the bat.  While we are allowed to have a “type,” unnecessarily specific expectations have the potential to sabotage our success around dating.

Judgements can certainly have a helpful function, and come from a part of you that is trying to protect your wellbeing.  If your gut is truly telling you that something about the date or your chemistry is “off,” there is no need to try and force attraction.

However, it would be a shame to miss out on an amazing person because you are getting hung up on their choice of shoes or a couple corny jokes they made.  In fact, you may learn to even find those innocuous “pet peeves” about your potential partner endearing and part of what makes you like them more.

You are not acknowledging what matters most to you in a relationship

You owe it to yourself and to your potential partners to have an understanding of your compatibility needs when it comes to values, personality traits, and overarching goals in a relationship.  We live in an era with constant conflicting messages around what we should be looking for in a relationship, whether it be from family, social media, mainstream media, or even friends.

A surefire way to sabotage your dating success is to be untethered to your needs and desires and to chase what others think would be best for you.