Should I Date Him?

Got a date lined up for the weekend and asking yourself, ‘should I date him’? Consider our pros and cons of potential mates.

should I date him


My first boyfriend arrived on the scene when I was just four years old. His name was Timmy, and he was the irresistible redheaded son of my grandmother’s neighbor. Those who know me can attest that I’m currently dating a strawberry-blonde (though he refutes the red cast) so I like to think that even at a young age, I knew there was something pursuit-worthy about a man with a crimson mane.

The relationship ultimately fizzled when Timmy moved two blocks away. It was a decade until my second shot at a boyfriend came along. Since then I’ve found my way in and out of nearly two dozen relationships (length and significance spanning a wide spectrum), learned my way through a laundry list of different types of datable men, and finally found the man for me.

What I’ve discovered is that meeting the guy of your dreams could happen any number of ways. There’s no predicting if he’ll be a neighbor or a stranger and no way of determining with absolute certainty which holds better odds for long-lasting love. With that said, here are a few different types of dates I’ve personally encountered and what I’ve learned from each. Next time you find yourself asking “should I date him,” take these pros and cons into consideration!


1. Dating the Cute Neighbor

should I date him

  • Pros: Convenience! It’s great to know that he’s only a step away to be at your beck and call.
  • Cons: Eventually realizing that your relationship is built on convenience vs. sustenance, the awkward confrontation after its ends, and the risk of catching him with another girl post-breakup.


2. Reeling in Love Through Reality TV 

should I date him

  • Pros: The chance to meet a complete stranger with limitless potential, really living in the moment, and knowing that no matter what you will have a great story to tell.
  • Cons: Realizing that anyone who gets cast on a reality TV show is somewhat crazy, yourself included.


3. A Sizzling Summer (or Spring Break) Fling

should I date him

  • Pros: Knowing that its fleeting makes every moment hot and heated, not having to make a commitment to anything more than having fun, having an amazing fantasy to always look back on and to make your girlfriends back home totally envious.
  • Cons:  This can go one of two ways: 1. You might think that you’ve actually fallen in love in which case you have to face the reality that distance will always keep you apart, or 2. You never see the guy again but realize that, thanks to your lusty romp, you’ve brought more than sand home from vacation.


4. Matchmaking While Networking

should I date him

  • Pros: This is one of the easiest ways to meet a man because you are both looking to meet new people, you know you have something in common, and it’s totally acceptable to exchange numbers.
  • Cons: Falling into the trap of hooking up with someone who would’ve benefited you more as a business connection than a love connection.


5. Courting Your Classmate/Coworker

should I date him

  • Pros: Knowing you have common interests, common goals, and likely a similar group of friends, conveniently having time scheduled to see each other, getting to turn home work time into hook-up time.
  • Cons:  The inevitable distraction it will become while on the job, the interoffice gossip that’s sure to arise, and having to still working collaboratively even if things come to a nasty end


7. Finding Love in the Club

should I date him

  • Pros: You probably had a great night when it happened, you know the guy is fun, you know you like to hang out at the same places.
  • Cons:  Everything, if he’s taking you home tonight then he’s probably taking home another girl every other night; you’re not special, you just happened to be around.


Needless to say there’s a great story to tell behind each of  these encounters. In the meantime, we’d love to hear from you! Have you ever asked yourself “should I date him”? How did it turn out and what did you learn?


Happy Dating!


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