First of all (and this is especially for the brand-new midlife bachelors out there) recognize that flowers don't make the man. This means that if a woman doesn't like you, then sending her flowers is not going to magically change the situation. Better to save your money! Flowers are an enhancement, not a means to a better relationship.
When to Send a Woman Flowers
1. Send her flowers for a special occasion (birthday, anniversary, Valentine's Day, etc.) The most common special occasions for flowers are birthdays, anniversaries, and Valentine's Day (of course). You might want to mix in some balloons, too, if she likes balloons, that is. If she works in an office, be sure that you have them sent via a reputable florist (and not self-deliver some store-bought bouquet) - as the show at work in front of her colleagues is just as important the flowers. Trust me on this one! Oh - if you don't have a girlfriend on Valentine's Day then please read this other article here entitled, What to Do on Valentine's Day when you Don't Have a Date.
2. Send her flowers when you have misbehaved, and need help emerging from the doghouse. Flowers won't get you out of the doghouse entirely, but sometimes they help just a little. Remember though that if your relationship is falling apart, then don't waste your money on flowers ... flowers don't make the man! Remember that!
3. You could also send something sweet IN ADDITION TO or INSTEAD OF Flowers such as a flower / chocolate-covered berry combination ... with or without wine, etc. All of the same rules and reasons outlined here apply to this type of gift - which are considered to be gourmet Valentine's Day type gifts.
4. Balloons are also an option - they are a little less serious, and more fun than flowers.
How Many Flowers Do You Send?
Don't go overboard. One of my old buddies used to send two or three dozen red roses to his girlfriend ... and it was completely unnecessary ... especially because she thought it was weird (because he was unemployed at the time). Flowers don't make the man! I know I am repeating myself with that phrase but I'm really trying to prevent some subset of you out there from doing something excessive and unnecessary. So what is the magic number of flowers to send? Maybe a dozen if you are sending roses, or maybe something similar in size if you are sending something else (like balloons). Make sure they are in a vase, too. You also need to consider where you purchase the flowers from. If you want ease of delivery, you can order them from an online florist. I usually use a local florist that I am already familiar with.
What Kind of Flowers Do You Send?
Remember - red roses mean love, yellow roses mean friendship. And I forget what other colors mean - so best not to use them if you don't know either. Don't send yellow roses to someone you are interested in because I guarantee you she will think you just want to be friends. Women are way into symbolism ... stuff we as men would never think of, or care about. Now some women (for whatever reason) don't like roses ... you have to really know the woman in order to know what kind of flowers she prefers. If you don't know her well enough yet, then send red roses - and listen carefully to what she says the next time she talks to you ... which means that if she goes on and on about how nice they are, then she probably likes roses ... or if she just says "thanks", and starts talking about something else then you know the roses made a minimal impact on her. Okay - now here is a curve ball ... one of my female friends would rather receive a plant than flowers ... perhaps because cut flowers die off within a few days ... versus a plant which can grow like your love or your relationship (barf)? Okay so that was a bit corny, but you get the idea - every woman is different.
Just as you must know WHEN to send a woman flowers, it is equally important to know WHEN NOT to send a woman flowers ... and that is the subject of the second part of this article, When NOT to Send a Woman Flowers
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