Dear Judith,

Well… where to start? I’ve been in love with the same guy for 3 years now. He is a good friend with my brother too. I only see him when my brother lets me tag along with his friends… as much as I want to see him more and more.

What I need help with is… I want to tell this guy how I feel about him and get it off my chest… but without it being awkward. What should I do?

In Love

Dear In Love,

Your brother won’t arrange an introduction? What is your relationship with your brother? Are you friends or competitors? If there’s some friendship between you, ask him his opinion of his friend and whether he’d support you in getting to know his friend (if he’s threatened or against it, it would make it much harder for you to make a connection with said friend.)

Your brother would also be in an unique position to know this young man’s character: morals, the way he treats and talks about women, his honour and honesty — these are invaluable insights your brother would have into his friend. It’s not uncommon for a guy to have friends he wouldn’t think of letting NEAR his sister!

A caution here, as far as “telling him how you feel”; LOVE is a state of being that comes with time, through truly knowing and being known by another person. Not at all to diminish your feelings for this guy, but honestly dear, when you haven’t spent a significant amount of quality time together, please don’t go for the “L” word. If you get a positive, heads-up report from your bro, then try showing him the lowest key of interest you can find and let him pick up the bait if he’s interested. Be your most attractive self, not a “tag-along” little sister, but a lovely young woman in your own right! GOOD LUCK!

Sincerely,

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