How to Handle an Awkward Date

It has probably happened to many of us.

You go on a first date that doesn’t go as well as you hoped. Maybe you know instantly that there’s just no chemistry. Or it starts out fine, but things quickly go south. 

Years ago, my buddy Lee and I took two girls on a double date to an Italian restaurant. We liked them and things were going well. Conversation flowed easily and we all laughed at each other’s jokes. 

What Lee and I had not planned for was that our dates ordered an enormous amount of food—appetizers, main courses, drinks, desserts. We were college students at the time, so we weren’t exactly swimming in cash. 

When the bill arrived, Lee and I swapped a look and realized we didn’t have enough to pay the bill. 

For some reason, the restaurant didn’t take debit cards. I nudged Lee, then looked at the girls. “Excuse us, we’re gonna run to the restroom for a minute,” I said. They smiled and nodded as we stood up.

Lee and I snuck out of the restaurant, jumped in our car, and drove to an ATM to get cash. We returned nearly 30 minutes later. The girls stared at us awkwardly, thinking we’d been in the bathroom for half an hour. 

We paid the bill in cash. When we walked our dates back to the car, they noticed it was parked in a different spot from when we arrived. They knew we had bailed in the middle of the date to make a cash run. 

It was not our shining moment as bachelors.

Needless to say, any romantic future with these ladies fizzled.

Another time, a friend took a woman out to eat. Her 10-year-old daughter joined them. They had met at church, so at one point the daughter asked my friend: “Do you like Jesus?”

“I love cheeses!” he responded. “Especially brie. And Jarlsberg. What about you? Do you like cheeses too?”

The little girl and her mom stared back. 

“No, I said, ‘Do you like Jesus?’” the girl clarified.

Oh. My pal shifted awkwardly and said he did indeed like Jesus. But the social faux pas had already been committed.

Despite our best efforts, sometimes we say or do awkward things on a first date.

Or, as mentioned earlier, we know right away if there’s no connection and the date isn’t going anywhere. What do we do in those situations?

My friend Jason had one solution. A few minutes into a rocky first date, he simply blurted out: “You know what? Why don’t you just go? I’ll get the check.”

The lady was relieved, but she tried to be gracious. “Are you sure? I feel bad.”

Jason assured her it was okay, so she gathered her purse and left. Jason paid the bill and that was the end of that.

Jason’s approach feels a little harsh, but at least he was honest. Neither of them wanted to be there, let alone waste the next few hours struggling for small talk and feeling uncomfortable.

My suggestion for handling an awkward date? It’s the same as handling any other situation as a Christian and a decent person. Be gracious. Treat them the way you want to be treated. 

Treat them as a fellow human, even if you both know you’re never going to see each other again after the night is over.

Unfortunately for us 21st-century daters, Jesus never wrote an instruction manual on how to handle a first date.

He did, however, tell us: “Do to others whatever you would have them do to you” (Matthew 7:12). That’s good advice for any situation, including how to bow out of a bad date.

Sacred Scripture gives us this advice: “Love one another with mutual affection; anticipate one another in showing honor.” (Romans 12:10)

“If possible, on your part, live at peace with all…” (Romans 12:18)

“[And] be kind to one another, compassionate, forgiving one another as God has forgiven you in Christ.” (Ephesians 4:32)

“Do nothing out of selfishness or out of vainglory; rather, humbly regard others as more important than yourselves, each looking out not for his own interests, but [also] everyone for those of others.” (Philippians 2:3-4)

“Put on then, as God’s chosen ones, holy and beloved, heartfelt compassion, kindness, humility, gentleness, and patience, bearing with one another…” (Colossians 3:12-13)

“Give honor to all…” (1 Peter 2:17) 

Whether at home, at work, or on a bad date, we need to follow Scripture and Jesus’s way in how we treat other people. 

That blundering, bored, unpleasant person across from you may not be right for you, but he or she is still a beloved son or daughter created in God’s image. 

So, if your date is willing, graciously sit through your meal or movie or concert.

Recognize they are simply looking for love, just like you are. Be kind, friendly, and wish them well as you part. Say a prayer for them that they will be okay and find the love they’re looking for.

Then move on with a clear conscience, knowing you treated them as Christ would. Look forward to better dates in the future. Trust that God will lead you to someone who is best for you. It may take some awkward dates to get there, but be gracious and loving along the way.