Well, you might start with asking what she wants to do with her future. That would give her a chance to drop hints as to whether that does or does not include you. If it is ambiguous…“I’d like to find a nice man and settle down and have children”…you can ask, “Do you think I might possibly be that nice man, or would you rather keep me in the friend category?” The main idea is that you are asking what she wants and listening to what she has to say, rather than putting it in terms of what you want…this is always charming.
If she skirts the question you are interested in, you can be a bit more blunt, “You are so bright, I think you’ll make a fine lawyer. Have you decided whether you are interested in settling down, too?” That is, be careful not to make it sound as if you think a professional career and marriage might be incompatible–like saying, “That’s great, but what about marriage and children?” unless that is what you do think. We professional women can be overly sensitive on that point, on behalf of others with different goals than we have, even. Just know that this is one potential minefield in your way.
If it is unambigous, you can slip in your side as a joke, “Oh, shucks, not getting married? I could have gotten my hopes up for someone like you! Well, you will make a fine religious, I’m sure. If I’m going to lose a woman like you, let it be to Jesus!” In that case, she will be relieved to not have lost a friend when the process of discernment makes her want to keep everyone she can.
If it is along the lines of, “I feel like I’m still on the rebound” or “I still have strong feelings for someone who doesn’t reciprocate”, then you might say: “You are a wise woman, and an honest one. I’m glad you were frank with me about that. If you would like, though, we can still go out for Valentine’s Day, just to someplace very UN-romantic. It’s up to you.” As long as you are not a doormat and make your possible interest in something more serious clear, being a true friend when a woman needs one is not a bad way to move up to better things later on. If she holds you as an “I like you, get back to me” then stay in the “I like you, and if I’m still available, then sure, feel free to get back to me” category. You don’t have to shut the door to let her know you aren’t feeling a necessity to keep it open for her. Fair is fair.
If she sounds as if something serious with you might be a possibility in her future, you might say, “Well, it is too soon to talk about marriage, after only 10 weeks, but for this year, would you like to be my Valentine?” If so, you can make plans for a more romantic outing than you’ve had in the past. If not, she’s only turned you down as a Valentine. That is something you can cope with in good humor without ruining the whole evening…“Well, you will make someone a fine catch, and I didn’t want to lose you for having not asked!” Either way, you want to be a guy interested in finding a woman, not a stalker. Make it totally OK for her to be just as interested as she is, and not one bit more. That is very attractive, as it makes you seem both self-confident and genial. Do not make all this very serious; that can be scary.
If she doesn’t want to be your Valentine this year or any other, you’ve given her a chance to let you know how she feels without putting her in a position that she has to reject a stronger declaration on your part. She’ll appreciate that, I think, no matter how she feels about you.
Whatever you do, do not lay a big guilt trip on her about your feelings. Do not act as if she is your last chance on the planet for marital happiness. That is creepy and off-putting. (And thank goodness, it sounds as if it is not true.)
That is the nice thing about Valentine’s Day. It is something that gradeschool kids celebrate. It is not a lifetime commitment, just a day to celebrate the joys of simple affection and an excuse to buy chocolate. It doesn’t have to be more than that. Use that to your advantage!