So recently someone I follow was falsely accused of sexual harassments and would of probably lost their career if not for what essentially comes out to luck (the accuser was found to be lying). What caused this? Flirting through the wrong medium.
I strongly believe these 3 situations are the only way men should flirt, and in doing so we can create a better environment for everyone. Note: this advice only applies to men flirting with women. The reverse is not true (women flirting with men) or with men flirting with men.
Scenario 1- Online Dating (OLD): This one is self explanatory, but you can (respectfully) flirt in OLD with little negative side effects. A few things to note, treat women like heterosexual men until they get to know you better (no dick pics, no overly sexual first messages, etc.) If she is very flirty and get sexual first then you can go there (but in my experience this is rare). As guys we can see a women (or another guy) we hardly know and want to pursue something, most women do not work that way.
Scenario 2- Bars and other similar social settings: There are certain social situation where you can flirt with women, and it even is encouraged (eg: singles night or speed dating). The rule of thumb would be a place where the leisure is the primary incentive to go (bars, parties etc.). So for example, a grocery store is a no go, that is because most people are not actively seeking a relationship there.
What if she is giving you signs she is interested in a place like the gym or grocery store? NO. In most cases she is just being friendly (this is 99.8% true if she is being paid to be friendly, such as a waitress or cashier). If she has an interest in you, let her make the first move but trust me you do not want to be that person who makes people uncomfortable. Always be friendly and cordial, but remember our rule, treat her like a heterosexual man until she get to know you (see scenario 3).
Scenario 3- Someone you have know for a while: Say you have a classmate who you spend time getting to know over a semester of organic chemistry, can you ask her out? Yes! But please keep a few things in mind. First, make sure you actually know her, and you guys can converse freely washout any awkwardness. Second, this will change the nature of your relationship, you cannot put the cat back in the box. If she rejects you, you may just lose a friendship (but in my opinion I think the pros are always worth it). Finally, don't let yourself be strung along. This is perhaps my most important advice, I would take anything that isn't an enthusiastic yes as a no! (this doesn't mean she has to want to go on the date rights now, but that she clearly wants to go on a date when you both are available). She may try and change the subject or give a half answer, whatever really. Anything that isn't an enthusiastic yes is a no, and you should start looking elsewhere for romance.
As always, be respectful and remember that there is always another women, never get caught up perusing one women who isn't returning your feelings. Being persistent only works in movies, if she rejects you or isn't interested MOVE ON!
Good luck~
Edit: To clarify, this post is about how I believe men can maximize success while minimizing risk. A lot of women replied with how they like or had men approach them in various public settings but I think you fail to put yourself in the guys shoes. Chances are walking up to random women at a gym or grocery store are not going to work out and can even have risks (no one wants to be the creepy guy at the gym hitting on women). I do not think men should be taking those risks, when the alternative is better, safer (for women especially) and more likely to succeed.
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