10 Dates You Should Go On If You Really Want To Know A Guy

Coffee and movie dates are OK, but don’t set yourself up for a shocking bait-and-switch when the honeymoon phase ends. If you want to reveal his true colors sooner, you’re going to have to put him to the test. Here are 10 ideas to save you the future heartache and draw out what you’re really working with.

Somewhere you know he’ll have to wait

If you’re looking for someone with potential to last ’til death do you part, chances are you’ll eventually run into that ‘in sickness’ line of the vows. You don’t want to find out the hard way that who you thought was the apple of your eye is really an immature man-child during an unexpected 12-hour emergency room stay. Real life isn’t always fun and games. You may need to sell him on going to a large theme park on the weekend and getting on the most coveted ride to see how he handles himself during the delay.

Something outside of his comfort zone

Unexpected guests always seem to drop by at the worst times, especially your favorite aunt, Flo. If he can stand in a line outside Game Stop for hours waiting for a midnight release of the next Call of Duty then he should be able to make a quick daytime run to the local pharmacy for some feminine hygiene products. Why not try a date at a Paint & Sip studio and see if he’s willing to let down his macho guard and find his inner Picasso while enjoying a Cabernet with you?

A restaurant

Wait, what happened to the non-traditional ideas? Stay with me here. A restaurant may seem typical, but you can tell a lot about a guy from this. Pay attention to how he talks to your server. He’s there to impress you, so he may still treat others around you with glimpses of his true character. Don’t let a guy get away with promising he would never disrespect you like that because you’re his lady. If he’s rude to one person, he’s capable of being rude to them all.

Something competitive

There’s a lot to learn from a healthy competition. You want to know ahead of time if he’s OK with letting you shine. A guy who’s insistent on being at the top all the time may not be someone who wants to meet you on your level and be attentive to your needs. He also may get jealous if you start getting more promotions at your job or even earning a higher salary than him. If he’s too busy challenging you, he won’t be focused on connecting as a unit. Get ready to lace up those bowling shoes, ladies.

A group date

Our friends can be the absolute worst for ratting us out, but you can use that to your advantage by trying to get his friends around. If he’s trying to put up a front for you, they’re going to call his bluff. You can also see what type of people he’s around when he’s not with you. They say birds of a feather flock together so if his buddies seem sketch, I’d proceed with caution.

Something super simple

It’s easy to enjoy yourself at a date that’s mostly set up for you to have a good time. If you two wind up getting coupled up for real then the dates may start coming few and far between with more low-key at-home lounging nights instead. You want to know he can still be enjoyable company when things are chill and even if he’ll put the extra effort to be creative with a plain arrangement. How about a picnic in the park?

Something in his element

So, this guy really likes you and he’s passed the self-giving dates with ease, but don’t let him off the hook just yet. If he’s hiding any obnoxious character flaws, he can only keep the momentum up for so long. Instead of pulling him away from his daily workout session at the gym, go with him! See if he lets the mask down when he’s in his zone on his familiar stomping ground.

Something where you need to work together

You ever have the feeling you’ve been single so long, you wouldn’t even know how to incorporate someone into your routine again? I’m sure guys go through the same, but you need to know there is at least potential he’ll be able to shake off some of his set-in bachelor-for-life ways. If you have an athletic bone in your body, why not try an obstacle course event like a Tough Mudder? If not, escape room dates can also be fun to show team building skills as well.


Confession: I got this idea from The Princess Switch. However, the movie demonstrates it all! It’s important to see if a guy is willing to self-sacrifice for the right reasons. Is it all for show or does he actually have a kind heart behind his smooth talking, cool under pressure, testosterone-fueled ways?

A dating class

All serious relationships go through their roadblocks. Will he be willing to constructively work on things when it does? Or will you get a hard no every time you bring up couples counseling? It may sound like a lot for someone you’re just dating, but if you’re looking for a guy to get serious with eventually, you should know he is going to be able to put in an effort to make it last. You never know, you might learn something helpful for you both!

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