DEAR EMILY,

I’ve known this man since I was 10 and he was 15. I am now 27. He’s my eldest brother’s best friend and classmate from elementary through college. He’d sleep over on weekends, and vacation with us here and abroad—that’s how close he is to our family. He has an older married sister he is not close to.

My mother privately hopes that we will eventually marry, which my brother finds amusing. I like him in a confused way, and he has not made any move to show his interest in me. My brother is married now, and his friend just goes from one girlfriend to another and is never serious with anyone. Aside from a company these two friends put up, they have also founded a small charity.

I work in a publishing company, and lately, someone from my office has started to court me and my friends are pushing me to give this guy a chance. He is nice, hardworking and really into me.

The problem is, I’ve been in love with my brother’s friend since I was young. My brother’s friend teases me constantly, and calls to say hi all the time, picks me up from work if he is “in the neighborhood,” which is quite often, but has said nothing serious to me.

When he learned of this suitor, he said I was “too young” to be getting serious, and should take my time about marriage. He cautioned me to open my eyes to other “possibilities.” He shows his concern like a brother, but as to his feelings, why isn’t he doing anything about it?

Should I be forward and declare my love for him?

PERPLEXED

If you’re a fan of Jane Austen’s novels, her heroines would rather die than divulge their feelings to the men they love. That was the milieu then. But today’s operative word is openness—where affairs of the heart are bared and blared on Facebook or Twitter, and dating is not confined to having coffee or going to the movies.

If Paul Simon can sing “50 ways to leave your lover,” there can also be more than that to ensnare one. But pouncing on him is definitely a no-no. Instead, you may try using your feminine wiles ever so delicately—like whispering, as a courtesan once said.

Talk to him just above a whisper and this will snap him out of his stupor, and definitely get his full attention.

Something is probably happening to him, too. How else to explain why he is telling you not to be serious about marriage at the mature age of 27, or cautioning you to be open about other “possibilities?”

Could the appearance of a rival have something to do with his subconscious seeing reality unfolding? That this girl who has remained young in his mind has finally blossomed into a woman?

Entertain this suitor and let this family friend discover there’s a serious new kid on the block who can snatch you away from him.

You may have been in love with him forever, but if your feelings have remained unrequited, aren’t you being unfair to yourself? Couldn’t you miss out on other possibilities for true happiness?

Are you going to brush off this guy who is really into you—and wait for something that could be nothing but just a mirage?

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