Knowing when to send a woman flowers is just as important as knowing when NOT to send them.  Through my own trials and errors over the years … plus having watched many of my friends struggle with this same issue … I think I’ve put together some good bachelor guidelines for when to / when NOT to send flowers, how many to send, what kind, etc.  I also included some direct input from some female friends of mine, too.  Here you go …


There are five sections to this short article:

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]
  1. 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!
  1. Send her Flowers the Morning after the first time you have sex with her (assuming you want her for a girlfriend).  I have done this a number of times in my past – usually send roses with a card that simply says something like, “I enjoyed last night, and would like to see you again soon.”  Then sign your name, of course.  I’m told that women think this is way hot – so now I’m passing this secret on to you.
    1/1/2013 UPDATE – I have since reconsidered giving the advice about sending flowers after you first have sex – and I now think sending flowers after the first time is a VERY BAD IDEA.  Why?  Because it is totally unnecessary PLUS if you do send flowers too soon, you might unintentionally be granting her the “power” in the relationship … meaning that she may think that she’s the one in control of the relationship.  You never want to grant a woman that kind of power – certainly not right out of the starting gate.  So my advice has evolved (some will say “devolved”) … but I definitely now think you should not send flowers too soon.  Better to keep the “send flowers card” in your back pocket, and do so when it is more appropriate.
  1. 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 gifts.

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.   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.

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.   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 (Serena) 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?  Okay so that was a bit corny on my part but you get the idea … every woman is different!

When NOT to Send a Woman Flowers
Just as you must know WHEN to send a woman flowers, it is equally important to know WHEN NOT to send a woman flowers:

  1. Don’t Send a Woman Flowers During a Breakup.  Don’t throw good money after something bad.  Flowers won’t save a relationship.  The only possible exception might be if the breakup is being caused by one of you moving away (like for a new job or similar).  Otherwise you risk being viewed as pathetic for sending flowers to a woman who wants nothing to do with you.  Keep your self-respect – and save your money!
  1. Don’t Send a Woman Flowers Simply to impress her – sets a very bad precedent.  One of my buddies just loves to spend big on new women he goes out with.  He sends them flowers … takes them out on limo rides for their dates … and he is not super-rich mind you … he makes maybe $100K/year.  Anyway – these women come to expect a lot of flash and cash from him … and although he seems to haul in some pretty cute women, none of them stay around very long because it is all just a show.  My advice – send flowers for a specific reason only … not simply to impress her.  Unless you have money to burn, of course!
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About the Author

Midlife Bachelor chronicles lifestyle, dating, and relationship experiences and advice to avoid a midlife crisis. Readers like you are often beyond young adulthood in their 30’s, 40’s, and 50’s that want to understand how dating, sex, relationships, and love fit in with our lifestyles.