Query: There’s this boy who’s my friend. I like him a lot. But as more than just a friend. He doesn’t know. I want to tell him soon because I can’t stop thinking about him. So I’m planning to tell him on Valentine’s Day. Is this going to mess up our friendship? Should I ask my mom to send me to another school so I don’t have to see him every day? Am I a stalker? I feel so much love and intensity for him.

–Longing in Limbo

Carrie: There’s no risk so great as sharing the depth of your feelings, whatever kind, honestly and openly with another. There’s nothing so rewarding as finding that the person with whom you’re sharing wants to share as deeply with you in return. For some people, these connections come naturally. For others, complications abound: the right person at the wrong time (he likes you back, but his parents are moving across the country); the wrong person at the wrong time (the boy you like has a crush on your best friend); the wrong person at the right time (he doesn’t feel deeply for you, but is interested in learning to use his relationship skills).

For the sake of your own self-respect (a hard concept to apply with consistency in adolescence, but practice makes perfect), tell your friend how you feel. Even if he doesn’t/can’t return your feelings, you’ll have done your best to honor your emotions. Certainly, you may not have the same friendship with him ever after, and may lose contact with him if he feels uncomfortable after your revelations. But won’t knowing one way or the other be a great relief? Good luck on Valentine’s Day.

(P.S. Boys don’t generally understand/remember/apply the significance of Valentine’s Day in the same way that girls do. Don’t be surprised if he has no idea why you’re bringing up this topic on that day.)

Query: I’ve been with a wonderful woman for the last three years or so. She’s at that age where she’s facing the issue of whether to have kids before it’s too late. I get the feeling that she’s expecting me to pop the question this Valentine’s Day. Then she’ll want us to "settle down" and do the Ward-and-June thing. I’m not so sure about any of this. I haven’t met anyone whose company I enjoy more than hers. But I’m not ready to do the married-with-kids thing–even with her.

–Nervous near Niagara

Carrie: She’s wonderful. You enjoy her company more than that of any other human of your acquaintance. And you still don’t see yourself feeling attached enough to her to try out formal partnering and parenting? Then take advantage of the upcoming holiday and break up with her, or lay your cards on the table and see if she’ll hang around despite your inability to commit.

You could get lucky. There are all kinds of women out there with self-esteem damaged enough that they’ll stay in unfulfilling relationships in hopes of change or growth on the part of their partners. In which case, your announcement will only serve to make her try harder to get past your reserve.

Or maybe you’ve read the situation through the distortion of your own fears. Maybe she doesn’t want the kids and normal, formal sanctification of marriage. Maybe she’s no more attached to you in any permanent and irrevocable sense than you are to her. But you’ll never know if you don’t talk to her.

Query: My girlfriend’s best friend says that my girlfriend expects me to do something spectacular for Valentine’s Day. She says that my girlfriend breaks up with boys who don’t show their appreciation with enough imagination and devotion (and cash). What should I do?

–Broke on Boyd

Carrie: Here’s a handful of options. 1) Go to a pawnshop with the best friend to pick out an affordable chunk of bling-bling for the young lady in question. 2) Consult with the best friend then prepare a romantic, homemade gourmet meal for two. And don’t forget to bribe your family to leave the premises while you’re dining together. 3) Tell your girlfriend’s best friend that you’ve never stayed with a girlfriend yourself who didn’t show you a good time, from the depth of her heart, on the sacred occasion. 4) Given that you’re spending all this time with the best friend, maybe you’d better reevaluate where you’re putting your energies–the best friend may be a better option.

Whatever else you do, do not spend a big pile of money on this person. People who judge others by the size of their bankroll do not make good emotional investments for the rest of us. If you put time and thoughtfulness into your Valentine’s Day message of love, that should be more than enough. If it’s not what she wants, then she’s not what you want. Which brings us back to the best friend....