Dating Should Be Fun (And, If It's Not, Here's How to Change That)

Are you taking yourself too seriously?

Dating can be very serious business for a Catholic who is not looking for hookups or a weekend fling, but for a lifelong partner. For someone looking for a spouse and not just “hanging out” dating can take on all the somberness of a job interview for your dream job. All the pressure. All the anxiety. All the uncertainty.

And while I am not encouraging hookups or empty relationships that go nowhere, I would also like to encourage you to remember that this is supposed to be fun. Dating is supposed to contain at least some element of lightheartedness. After all, you are looking for a lifelong partner and life contains a lot of humor. If you can’t relax and let your hair down with someone, no matter how good they look on paper, that might not be your match. I propose we put some of the fun back in dating. Here are five things to keep in mind:

1. It’s not a job interview, so put away your (mental) clipboard.

Yes, you may want to know their views on foreign policy, the electoral college, should the Western Church fast like the East, should moms stay at home full-time or work outside the home, or the local school debating instituting Critical Race Theory—but maybe not on the first date. Rather than looking for their positions on a variety of issues, maybe look more for what kind of person they are. Issues will shift and change. Character is where it is at.

2. Plan activities that bring out your lighter side.

It can be especially fun to plan an activity at which neither of you excel or have much experience. Go ax throwing or take a pasta-making class. Something that puts both of you out of your element can be hilarious and put you on equal footing.

3. Take the pressure of yourself to be perfect.

It can be so easy to overthink after a first or second date. Did you look OK? Did you talk enough? Did you talk too much? Relax. You want someone who will like you for you, not for an image of you. If you just didn’t click, it is OK! No need to overanalyze it. It is also OK if you find a friend and not a spouse. Life is full of lots of different kinds of relationships that don’t end in marriage. It’s not failure, it is part of the process.

4. Get to know the friends of your date.

Double date with your date’s best friend! The inside jokes may be many but resist the urge to feel like a third wheel. Rather, get the skinny on those college shenanigans your date has only alluded to. Find out about that embarrassing night when they were camping as kids. Maybe the friend of your date will produce pictures of middle school or that Halloween costume everyone is still talking about. Learning about your potential partner’s life outside of the two of you can be so fun, and no one brings out our most fun selves like our longtime friends.

5. Let go of the structure!

Some dates can be structured with a clear goal (example: dinner and then a movie). It is also OK for some dates to be unstructured without a clear goal (example: let’s meet at the park and do whatever). Just as the human brain needs to be bored from time to time in order to come up with creative solutions or innovations, sometimes a budding relationship needs downtime.

That plan without a plan time may lead you to discover a new cafe, a pick-up game of basketball at the park, or how your friend interacts with strangers. Don’t be afraid to be a little aimless together and see where things lead outside of an imposed structure. This may not be an ideal first or second date, but if you are leaning into a deeper relationship, it is OK to just be together and see if the connection exists without help. Just set out to have a fun afternoon and invite your person along.

Play is important.

It is crucial to the development of children, and we don’t necessarily move on from this as adults. It may take a different form (no one has asked me to come over for a play-date in a long time) but the psychological need is still there. We need laughter, jokes, good-natured ribbing, teasing, and play.

We need moments when we, even briefly, forget about the bills, the goals, the clock, and lose ourselves in an activity—be it sports, a comedy show, a favorite hobby, working out. The world can stop for a moment, as we experience the very human experience of joy and fun.

This fostering of fun is foundational to what CS Lewis calls Phileo Love (Friendship). And while friendship may not be the meaning of life, it gives value to everything else in life. “Friendship is unnecessary, like philosophy, like art.... It has no survival value; rather it is one of those things which give value to survival.” (CS Lewis in The Four Loves)

It's all about joy.

Remember that in your search for your spouse and in your earnest desire to start your family, there should be joy along the way. Joy attracts joy. Fun multiplies. If you take this dating thing too seriously you may miss connections with some joyful people, who if they don’t become a spouse, could at least become a friend.

If dating has lost all its joy for you, maybe reframe your connections as opportunities for fun rather than an interview or a challenge to be overcome. 

Pope Benedict reminds us, “I'm not a man who constantly thinks up jokes. But I think it's very important to be able to see the funny side of life and its joyful dimension and not to take everything too tragically.”