First Dates That Won’t Fail

OK, there’s no guarantee, but these fun suggestions can ease the pressure and help you get to know that person you swiped right on.

We recently gathered stories of failed first dates in Colorado Springs — with some firsthand proof that not all of them go bad. Maybe sitting across from a stranger for a few hours while you eat dinner feels like too much pressure for a first date. And sitting next to a stranger for a few hours in the dark at a movie does not help you get to know someone — although Carrie apparently found a workaround. So what else is there to do?

Here are a few suggestions for first dates in Colorado Springs, or beyond, that could take the pressure off and help you get to know the real person you’ve swiped right on.

Test Their Trivia or Crush Some Karaoke

A lot of first dates happen at bars, but finding one that’s hosting an activity is a good way to survive the inevitable lulls in conversation. Trivia lets you test your date’s knowledge. Karaoke offers insight through their song choice — plus shows you they’re either a great singer or willing to make a fool of themselves. Go here, smarty pants.

Enter the Escape Room

We would normally never recommend locking yourself in a room on a first date, unless it’s an escape room. Does your date have problem-solving skills? You’re about to find out.

Goof-Off With Golf

A little friendly competition reveals whether someone can laugh at themselves or whether losing a round ruins their evening (or how much they gloat as a winner). At a certain age, we’d rather dodge a windmill than manage someone’s ego. If your skills are more serious, get ballsy on these Springs golf courses.

Take a Hike

If you want an active partner, find out whether they can keep up on a trail as well as in conversation. Pick a trail neither of you knows; then you can see how your date handles it if you get temporarily lost.

Paint and Sip

Maybe you’re not looking for an artist, but someone willing to get creative or try something outside their usual routine is promising. See if their painting skills explain the color combos they wear.

Explore a Museum

Wander the exhibits and find out whether your date is curious, thoughtful and capable of discussing something besides themselves. A little intellectual chemistry beats spending dinner explaining your jokes. Feed your mind at these Colorado Springs museums.

Want to ease the pressure? Keep in mind you’re not auditioning someone for the rest of your life. You’re deciding whether you want to spend another two hours — on another day — with them. Have some fun. See how they handle a little nonsense. And remember: “owns a trash can” is a reasonable standard.

Don’t miss these local stories of first date fails to see what you’re avoiding. And if you still need more ideas, check out our How to Do Date Night in Colorado Springs.


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Laura Austin Eurich and Carrie Simison
Laura Austin Eurich and Carrie Simison
Carrie Simison is a marketing professional who has called Colorado Springs home for over 25 years. Laura Eurich is a teaching professor in the Department of Communication at UCCS, where she teaches media writing and public relations among other subjects. Together, the two besties love to explore and celebrate the Springs and document their search for the perfect bloody mary on Instagram.

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