Want to Impress A Woman? Do This.

Want to Impress A Woman? Do This.

Spoiler: It mostly involves being your (best) self
10 things I hate about you

By Taylor Davies | Last Updated: Nov 6 2022 | 10 min read

Here’s the thing about me: I am an excellent inside source on what women like and how to impress a woman—especially when it comes to dating and relationships.

As it turns out, an adult life filled with dating comes with some perks.

And even though I’m an only child, I’m a generous one, because I’ve decided to spill the beans on what you—wonderful, thoughtful, well-dressed man looking to excel in love, life and work that you are—can do to impress a woman like me. So! SG is here to share ten guaranteed tips for making a memorable first impression (or reigniting a long-burning spark!).

10 tips on how to impress a woman:

10 things I hate about you


Classic advice with a twist, no?

Plenty of guys can tell a funny story, but if it’s a story or a moment that makes you laugh, too? Even better. You don’t need to be the most self-deprecating guy in the world (that gets old, fast) but just be willing to be in on the joke.

Men and women feel similarly about the push and pull between confidence and modesty—especially when it comes to storytelling and humor.

We all want to relate to each other and come across as impressive, so finding that balance through humor is key.


men's huarache sandals outfit

Time to hit you hard and fast with some statistics: 100% of women notice when a guy makes an effort with his outfit.

It’s just science!

The good news is, you’re already on ol’ Style Girlfriend, meaning you can tear through the archives before your next big date. Start here. And then maybe this? Ooh, don’t miss this.

You get what I’m saying.


My last boyfriend used to open the car door for me every time we’d drive anywhere. It was a small gesture but I’m telling you every time he did it—we dated for half a year—I got butterflies.

Old school manners seem to be disappearing these days, so use these little opportunities to set yourself apart.

Hold the door open and walk on the street side of the sidewalk. Go down the stairs in front of her and up the stairs behind her (in case she falls). Help her with her jacket on either end of the date, and pull her chair out before she sits.

And fyi, this behavior doesn’t have to feed into toxic masculinity if you don’t let it. Paying for dinner doesn’t mean she owes you anything!

Instead, consider actions like these as one more way of showing you’re tuned into her, like nodding and making eye contact as she tells you a story, or sharing your feelings in a vulnerable way.

Bottom line? Physical displays of manners are so attractive, and they make a woman feel appreciated and special.


couple, stylish couple, man and woman sitting on a bench,

One of the best first dates I ever had ended with me and the guy going through our Spotify playlists and calling out our favorite new songs.

I gained a bunch of new favorite artists that night, and we both got a peek into the other’s private life. (Your musical taste says a lot about you, trust me!)

You can try this tactic with restaurants, but be wary of sounding a little pretentious. I read The Infatuation, I get it.

Unless you want to whisk her away from the bar because she just has to try this late night soup dumpling spot—save the restaurant chatter for the next time you ask her out. (Show, don’t tell.)

But travel destinations, movies and TV? That stuff is always SO fun to talk about.


First dates can be a little stale. Going over the same introductory stuff over and over again gets tedious, and can very quickly diminish any chance of a spark.

An easy way to transition from covering the basics to getting below the surface? One simple tool: The follow-up question.

Here’s an example:

You: How many siblings do you have?

Your Date: Two—an older brother and a younger sister.

You: Oh wow, are you close with them?

On its face, this looks like a way to get her to be vulnerable—and it is.

But by being the first to ask a question that involves some thought and emotional reflection, you’re inviting her to do the same, and creating an atmosphere of openness and trust.

If you both allow yourselves share something real, something you can’t point to on a map or type out on a business card, you show your date that you’re an emotionally intelligent person worth getting to know further.

It’s worth pointing out here that impressing someone in a romantic context goes both ways—you shouldn’t feel like all the pressure is on you.

Women are constantly doing little things to try and impress you, too.


how to impress a woman

Here’s the part where I unfortunately have to put one particular guy on blast. He had everything going for him, and I was totally smitten.

However, anytime he texted me (which was frequently, like, multiple times a day very early in our courtship) it was just to “say” something.

He either had a story to tell about himself or just a random statement. I was all for the attention—until I realized it wasn’t actually me who was getting the attention.

By sending these texts he’d pull me into a conversation that was mostly one-sided. I’d engage him by responding, asking for details and laughing along—basically fluffing his ego on demand.

Yes, you’re funny. Sorry you don’t feel well. Cool story about your cousin.

Guys, all you have to do to win over a woman who is already at least a little bit into you is ask her questions. (See that little bit about vulnerability above.)

It comes naturally during in-person conversation, but it’s pointless to pretend these days that texting vibes don’t play into the overall health of a relationship.

Again, this is advice that can go both ways, you should be giving as much as you’re getting when it comes to communication.


how to impress a woman

Okay so I may be outing myself as a hopeless romantic, but I can’t even tell you what a lovely gesture it is to buy a woman flowers.

In all my years, a man has brought me flowers exactly twice.

The first time? When I was asked to prom.

The second was when an old flame was visiting New York and picked me up at my door to go for a walk and a drink.

I told him I’d meet him downstairs outside my apartment, but he insisted on coming up because he “had something” for me. It was a simple bouquet of daisies and I was floored.

Needless to say it was probably the best $7 he spent all weekend. (Wink, wink.)


Once upon a time I was in love with a man. I loved nearly everything about him—everything except his face and body hair management.

Look, if you’ve got a beard that your lady just loves? Great! Keep it looking sharp is all I’m saying. If she doesn’t? Take her feelings into consideration.

I once loved a man with a robust, manly beard. When he stopped trimming it toward the end of our relationship—after I had expressed how much I loved it shorter—I realized he was using it to put physical and psychological distance between us.

Bottom line? A little maintenance goes a long way.

And if you’re hairier than most—as in aggressive back and shoulder hair? It’s time to make a choice.

Either commit to a regular waxing schedule or leave it be.

Figure out a maintenance level that makes you feel good about yourself and seek out a woman who’s down with it.


image: NBC

With one guy, we had a whole secret emoji language, so texting took on a whole extra (and totally playful) level.

Another beau and I shared an obsession with Swedish Fish. We’d send them to each other via snail mail across oceans when either of us was studying abroad in college.)

Inside jokes are a solid way to create intimacy before ever being remotely intimate with someone.

They help establish a connection that transcends all those early dating questions that feel sort of like an interview, and, at least for me, are a sign that I could actually feel comfortable around a new guy.


So The Learning Trifecta ™ is something I literally just made up as I was writing this, but the more I thought about it, the more I started congratulating myself for being such a g.d. genius.

TLT, as we’ll call it, is simple, and it can be employed over time and at any point in a relationship. The three points of TLT can be deployed in any order, and repeated as many times as you like until you and me, lover, are dead in the ground. They are as follows:

  • Teach Me Something. (I’ve always wanted to be able to drive stick shift.)
  • Let Me Teach You Something. (You, me, the ski slopes? It’ll be fun I promise.)
  • Let’s Learn Something Together. (Pasta-making class, anyone?)

In my opinion, using TLT to impress a woman is a way not only to establish intimacy and trust early on, but also a fun way to keep things exciting and spicy long after you’ve lit the spark.

So there you have it, ten—relatively easy!—ways to impress a woman. Remember, with great power comes great responsibility: so use these tips wisely…and only for good.


Ready to boost your dating confidence with a wardrobe that makes you feel like a million bucks?

Book a 1:1 virtual styling session with a member of Team SG! Your stylist will help you update (or overhaul!) the contents of your closet. Learn more >>

Taylor Davies splits her time between NYC and Sun Valley. She loves writing about menswear, overpriced martinis in dimly lit hotel bars, and cross-country skiing. Not necessarily in that order.