Knowing how to flirt with a boy is a skill that is both useful and fun to learn when you're hitting the dating scene. You may think that it's completely different than how to flirt with a girl, but you'd be surprised at how similar the two can be.
Don't Overthink How to Flirt With a Boy
When learning how to flirt with a boy, one of the main differences in the vast majority of boys and men is that you don't need to be subtle - in fact, sometimes you shouldn't. Contemporary culture teaches men that they should not be "in touch" with emotional things, and that they should remain tough and aloof. Flirting with these kinds of men can be difficult, because it's hard for both of them to know that you are flirting and for them to show how they feel about it. If you give flowers to a woman, it's completely culturally acceptable for her to blush and smile and perhaps giggle. The same behavior in a man is something he is likely to be teased about - even though he's feeling the same way!
Likewise, just complimenting him - "I like the way that jacket looks on you, Michael!" could be meant as a flirtatious invitation, but he may not take it as one, simply because it is not considered "manly" to be concerned about appearances - instead, that's being "vain." You're much more likely to let him know you're interested in him if you compliment him on some piece of equipment he owns - his car, for example.
The Sensitive New Age Guy
Of course, the other cultural archetype of the contemporary male is the opposite of the man described above - the person who is taught to be in touch with his emotions, to appreciate things like romance and beauty and more. Don't think these men are any easier to flirt with - they've been taught that they need to NOT assume that a woman is interested in them just because she compliments them. While they may be more graceful in accepting the compliments, they are also likely to assume they are simply a measure of friendship - not an intent for romance, which is what flirting really entails.In either case, if it seems the guy is missing the signals that you're sending, it's probably best to simply come out and let him know, directly, that you're interested in him. Flirting is only a fun game if both people are playing, and if he knows for sure you're interested, it gives him the chance to flirt with you back.
The Danger of Miscommunication
Unfortunately, both of the stereotypes above (and they are stereotypes, with many exceptions) have a potential problem included with their assumptions and obliviousness to emotional signals: if they have a crush on you, they may take perfectly nice everyday politeness as being flirtatious. It's a well known phenomenon of someone not getting the subtle signals that "she's just not that into you." Again, in these cases, clear communication - occasionally extremely blunt communication - is the way to go.
The Finer Art of Flirting
Both types of men are generalities, and it's entirely possible - and hopeful - that the man you want to flirt with is not out of touch, that he can both read your signals and respond positively. If that's the case, flirting can be one of the most fun games a couple can play - whether it's on a first date or after decades of marriage.
1. Pay attention: Your first strategy of flirting is to pay attention. Notice what he likes to do, notice what subjects or TV shows or stores make him brighten up and smile. As you get an idea of what actually occupies his attention, it will help you figure out how to focus it in the directions and moods that you want.
2. Get him to pay attention to you: Start to plant little seeds of the things that he likes around you - drawing his attention. A good example would be noticing that he likes pumpkin pie - and ordering some pumpkin pie bath oil to set off the mood.
3. Be suggestive: Once you have his attention, begin to suggest things to do together - things that he likes, at first, to associate them with you, and then as time goes on he will associate time with you as being something he likes - regardless of what it is!
Once you reach the point where your flirting has succeeded in the goal of a romantic relationship, don't stop! Keeping that playful attention on each other, suggesting ways you can spend more time with each other - that will help keep your love fresh and alive no matter how long you're together.