What to Do on a Second Date

You’re going on a second date!

Congratulations. You obviously nailed the audition that is the first date (or at least didn’t flunk it) and now it’s time to see if there might really be a relationship here. The second date offers its own unique set of challenges, so let’s dig into everything from Catholic wisdom to secular advice to personal experience in order to give Date #2 the best chance for success.

1.) Start with prayer

Say the rosary, offering the date and its future (or lack thereof) to the Immaculate Heart of Mary. Or, if you’re not a regular rosary devotee, just do the Our Father/Hail Mary/Glory Be trifecta. God and the Blessed Mother can do a lot with a little, and the prayerful offering will do more than you realize.

2.) Plan the date

The secular resources on this topic have conflicting advice on whether to go super-casual or really big on the second date. But a common theme that comes up is the need to mix it up. If you did a movie on the first date, do something that will require more conversation this time around. If you spent three hours at a restaurant on the first date, try going to a concert this time around.

The purpose is to create a unique rhythm for the date, prevent yourself from automatically comparing it to the first one, and to see your new companion in a different setting.

In looking back at my own modest dating history, I can recall one instance of doing the exact same thing on the second date that was done on the first (meet for dinner). It didn’t go well. When my now-fiancée and I had our second date, we did something completely different.

3.) Write it out

You’re trying to discern God’s will, and a big part of that includes discerning your own thoughts and emotions, which may be quite combustible right now. St. Ignatius of Loyola left the world a treasure chest of understanding on how to discern the will of God, and a wise spiritual director will have you start with journaling.

So get out a notebook and start writing out your thoughts. It’s highly likely those thoughts may conflict. After a pleasant first date everything from your deepest hopes to your darkest wounds can get activated and send the brain all kinds of conflicting thoughts. The place to put those thoughts is on paper. At minimum, they’ll be out of your head. Ideally, you’ll see some common patterns recurring.

4.) Restrain your expectations

Part of our deepest hopes being set off is the tendency to let your imagination run one or two (or several) steps ahead of where the relationship is actually at. Maybe you’re imagining this special someone at a family event that’s a couple months down the line. You’re thinking about how well they’ll be interacting with your friends.

Take a deep breath. You’re still likely a couple dates (at least) away from actually moving into each other’s worlds. As long as you’re still in the bubble where it’s just the two of you, just keep the focus there and enjoy the process.

5.) Build off the first date

As part of your journaling, you’ll presumably have noted things that came up which you found compelling and want to know more. Keep those at the forefront of your mind for the second date and look to find out more—if nothing else, just as a means of getting the conversation started again.

Red flags are different. Because you’re on the second date, we’re presuming that these aren’t automatic dealbreakers, but just things that made you go “Hmmm…”. How you handle these will likely reflect how well the above point about managing expectations was handled.

If you’ve already got the person penciled in as your plus-one for your cousin’s wedding, you’ll probably want to rush the process of bringing closure to this red flag issue. Your mindset is more likely to be “Better find out right away.”

But if the red flag wasn’t a dealbreaker, it’s probably something that has some nuance to it. My fiancée later told me about something early in our relationship that raised her eyebrow, but under the advice of her mom, she just let herself get to know me a little more (and by “a little more”, I mean a couple more dates, not a couple more years).

She knew me a little better and could bring it up. And because she knew me a little better, my answer made more sense to her. She had more context about who I was and could understand more clearly.

5.) Work hard at relaxing

Yes, it’s contradictory, but sometimes the simple act of relaxing takes some effort. The first date is marked by both people feeling the need to be “on.” That dynamic is still present, but it’s not sustainable, and you have to be able to let your guard down a bit.

For me, when I’m wound up (which, to be candid, is most of the time), the professional advice I’ve gotten is to pay attention to my voice. I make a conscious effort to speak slower and softer. The result is that my emotions gradually start to follow my actions, and a little bit of calmness ensues.

Whether that technique works for you, or you need to try something else, do what it takes to slow your heart rate and just enjoy the moment.

6.) Get more Divine Help

The Catholic Church informs us that every single person has a guardian angel whose first choice of their existence was to love us and to watch over us. Get your guardian angel involved. Even better, ask them to connect with the guardian angel of the person you’re seeing and to lead you both down the way God has marked out for you.