Ask Annie: Should I dump my friend who refuses to set me up with a guy I like?

Nicholas Anastacio | Graphics Editor

Dear Annie,

I’m in love with this boy, but our mutual friend indirectly refuses to try and set me up with him. Should I dump this “friend”?


Dear DW,

Do you remember the PBS Kids’ series “Arthur?” His younger sister, DW, achieved notoriety for her stubborn and entitled nature. Just check out the memes of her rattling a wired fence with tinted sunglasses and touting her illiteracy as an excuse for breaking the rules. If a friend stood in her way, she would undoubtedly address the issue through direct communication. Explain how you feel.

Jenna Baer | Cartoonist

You do not need to “dump” your friend, but you do need to have an open conversation to discern why they hesitate to help you. Even when elementary schoolers breach each other’s trust, they’ll take a trip to the playground and resolve the issue.

After sharing what makes this crush special, listen to your friend’s piece. They may not feel obligated to orchestrate a romantic interaction – especially if you’re not close enough. In “Arthur,” the ambitious DW made the most of every opportunity, so follow her lead in pursuing the boy some other way. Find another mutual friend or – bold idea – approach him yourself.

It’s also worth considering this friend could be trying to protect you. Even the illiterate DW would take the hint that your friend may have doubts about the success of this prospective relationship. Maybe they’re trying to save you from venturing down the wrong path. Perhaps, like Arthur’s friend Binky Barnes, he only speaks in rhyme. Or maybe the boy just isn’t interested, and your friend is worried about protecting your feelings.

But if your friend already brushed off your request for a conversation, that could be a red flag that they don’t care about your feelings. While friendships may not need total transparency or cooperation, they do need compassion. Can you have a friend who is indifferent to your wants and desires?

If you decide to pursue the boy despite your friend’s reason (or non-reason), make your intentions clear to your friend before finding other avenues to seek him out. Blindsiding your friend who might be looking out for your best interests suggests you don’t value their opinion, and you already know how frustrating a friend’s discourtesy feels. Like DW, don’t fear being brutally honest when it comes to your priorities.

In breaking the news to your friend, be specific about why this boy is the apple of your eye to appeal to your friend’s perhaps dormant romantic side. Does he make insightful observations like Arthur’s classmate The Brain? Do his blue eyes remind you of Arthur’s best friend Buster Baxter’s vivid sweater? Sharing an unforgettable attribute about this boy with your friend may open their heart to playing matchmaker.

Don’t be those clichéd friends who have a fallout over a romantic interest. Before connecting with the boy, focus on communication with your friend. Ask them if they have time for a quick malt – and I know you can read that, DW, so go for it!

Get along with each other,

Facing a problem, yourself? Annie has answers. Ask away!

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