(Edited to make it more PG13 and less R/NC-17)
Some of my thoughts were echoed in of all places, a young Taiwanese air flight attendant’s facebook notes advising the older dudes who hit on her but got nowhere. She was basically saying that middle aged men either chased after her the right way or the wrong way. The wrong way is dropping serious coin and taking the date out to famous Michelin star restaurants, lavishing them with known expensive brand name gifts, and end up going home with just a tiny peck on the cheek. The right way to wow is to do it with more thought, wisdom, experience, knowledge, and care. Basically be a leader (and a gentleman), not a follower.
Be the one who refines oneself, get really knowledgeable and adept at something. Sniff out the best places, the obscure hidden golden delights that has killer intimate atmosphere and yet top notch culinary skills, the underdogs. Be the one who researches say, fashion… and impress a gal by not buying that Hermes or Fendi bag, but by finding some up and coming Italian designer who won awards in Europe but is not quite yet known here, but makes bags of outstanding quality (or shoes or whatever accessories etc) that rivals the brand names, and let the date brag to her friends about the nature and thoughtfulness of the choices. Set yourself apart from the rest of the herd.
OK this is a food board, so the impressing is through food and drink, not accessories. But you get the picture.
Or even if you must go the way of Michelin, find the way to maximize your experience. Could be a slight change in an order or side order that enhances the enjoyment, custom request, or if you know what pairs best in terms of beverages, make that happen and blow your date’s mind that way.
However going so far out of one’s way to impress a date at a ridiculously hard to get into Michelin place just seems too much of an overkill, especially the hoops that require to be jumped over.
At some point, going out on the exact day of Valentine’s Day is such an overpriced and expensive cliche (forced tasting menus that sometimes don’t make sense…cough cough Mister Jiu’s 2/14 OMG WTF did I just spend this chit on and why did I get beef chow fun at the greasy stir fry joint afterwards with a Tsing Tao that was far more satisfying?) . Your date should be mature and generous enough to just enjoy the moment and feelings, and be happy with say celebrating before (or after), and the venue doesn’t matter as long as the thought counted.