“Hey, like, my friend’s brother wants to let you know that he thinks your co-worker is cute.” What a loaded statement. If someone specifically seeks you out to fill you in on some budding attraction, that person isn’t merely mentioning it to you, you know, just ‘cos. On the contrary, you have just been involuntarily stationed as intermediary for two romantic hopefuls. Thus begins my ultimate annoyance – obligatory matchmaking. Alas! If only I had Cher Horowitz’s gleeful perseverance.

Some gifted individuals are practically matchmaking enthusiasts. Patti Stanger makes titular millions off of her intuition and tenacity to spread true love in waves across the affluent sea. So why am I so bothered to simply match up everyone’s schedule and meet up with friends for drinks?

To condense it to one word: pressure. If I can’t give these two what they want, have I failed? If one person loses interest midway but the other is still game, I have to either tell the truth or sugarcoat the crap out of it to avoid any gut punches to their self-esteem. This is also why I have learned to never initiate a possible romance myself – two people could seem like a great match, but my attempted rendezvous (coated in uncouth anticipation) could likely reveal that one is just not feeling it while the other is.

Don’t get me wrong — I love my friends. I want them to be merry and tickled pink forever and always. But once I’m thrown into the impossible task of orchestrating “hang-outs” and forcing conversation between two people with my approach soaked in awkwardness, I realize that I’m a damn good friend for trying to come off this natural. I want to quit relaying texts and giving fully-loaded biographies of each person to the other. I want these two to actively pursue each other themselves, forming an organically-grown romance. Is that too much to ask?

Nonetheless, I must reiterate that I love my friends. If the task is presented, I will try to please them to the best of my abilities. I’m not going to enjoy it, but all the awkward tension can prove worthy if my friends end up happy.

How do you feel about matchmaking? Love it or hate it?

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