Manly Skills

The Gentleman’s Guide to Approaching/Flirting with Women

Afternoon gents, it’s Max from The Young Gentleman’s Guide here! Today’s article is, surprise surprise, inspired by another article by Elena from A Vintage Athenian. In this article, Elena speaks about how the art of flirtation has evolved over the years. She gives some optimal advice for both young men and women to heed when approaching each other in the romantic manner. So today, I thought I would throw my hat into the ring and give you young gents some pointers on how to snag some digits from that certain woman.

1. Approach her in person

I’m sure we’ve all done or seen it before. Someone leaves a flirtatious comment under an attractive woman’s photo online in an attempt to woo her, which more often than not leads to nothing developing unless he then “slides into her DMs” as people say. Technology has no doubt played a huge role in how we interact with people, but it has seriously downplayed the art of flirtation. If you really want to win over a lady, you should approach her in person. Even if nothing develops between the two of you, you’ll still end up developing a better connection than you would just send messages back and forth on Facebook.

2. Be complementary, but not predatory

While the line between those two adjectives seems to be dissolving more and more as time goes on, a real gentleman knows the difference between complimenting a woman and acting like an animal. If you want to compliment a woman without being creepy or predatory, complement on what she’s wearing or how she has her hair done. Saying something like “That dress looks great on you” or “I love how you’ve done your hair” will be much more flattering to a woman than saying you like her breasts or her rear. While those two things can definitely contribute to how attractive a woman is to you, straight up commenting on her body like that can be incredibly demeaning, not to mention it just makes you look and sound like an animal.


3. Don’t be too pushy

This is probably the most difficult line specifically for men to draw. There are very few things to be admired more than a gentleman with ambition, determination, and persistence. That said, there is a difference between pursuing a woman and being pushy. If you’re pursuing a woman, you strike up a conversation with her and try to get to know her, but you also recognize if she’s not interested, and stop pursuing her then. Being pushy means that you keep trying to have a conversation with her even if she’s already made it clear, whether verbally or not, that she’s not interested. And there is no circumstance in which you should ever chase after her. By that point you’ll just appear to be desperate, and no one, especially a woman would find that attractive.

4. Just be yourself

I know this may sound like just typical bumper sticker advice, but even as cliché as it may sound, it will go a long way. You should obviously be confident whenever you approach a woman, but there is a huge difference between being confident and being fake. If you end up striking a conversation, keep it colloquial, and just talk about things that she might find attractive in you. In my case, I would most likely tell her that I play in a band. It’s simple, colloquial, and a lot of ladies might find that attractive. Just be confident, be yourself, and keep it simple.

So there we have it! I’m obviously not saying that all of these plans are completely foolproof, but I’m willing to bet that any of you gents who practice these things will end up snagging some digits before the end of the night! If there are any tips we may have missed, please let us know in the comments, send us an email at, or check out Elena’s article about this subject! In any case, I hope you enjoyed reading today’s article. Please be sure to share the article, follow the blog, follow The Young Gentleman’s Guide on FacebookTwitter, and Instagram, and support us on Patreon. And on that note, this is Max from The Young Gentleman’s Guide, and I’ll see you next time!

2 replies on “The Gentleman’s Guide to Approaching/Flirting with Women”

I loved it!! After each suggestion I was like “Finally someone said it!” 👏👏👏 Thank you so much for the reference Max!

Liked by 1 person

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