How to Impress a Woman Who Has Dated a Lot of Men

Don't try to outdo the men before you. A woman who has dated a lot has probably sat through the confident act, the mysterious act and the big-plans act already, and she can tell it from the real thing. What stands out is steadiness: you say what you mean, you do what you said, and you pay attention to her. Dan Bacon of The Modern Man puts the core of it this way: the secret to impressing a woman is to not try to impress her at all.

None of the pages we read say that the number of men she has dated changes the advice. What it changes is how much of the usual routine she has already seen, so the routine works less well.

Fake confidence is easy to spot when she's heard a lot of it.

• Instead of "I'm probably the most chill guy you'll meet," say "I had a busy week, so I'm free Thursday or Saturday."
• Instead of "Uh, I guess something chill but open and maybe long-term if it feels right," say "I want something real with someone I enjoy seeing regularly. I'm not looking to rush, but I'm also not trying to waste time."

If you like her, act like it. If you're unsure, say so. Texting heavily for two days and then vanishing for a week is the thing she's most likely to have been through already.

Effort looks like a specific plan. "Wanna hang sometime?" followed by four days of nothing is the weak version. "I know a great tapas spot near downtown. Want to go Thursday at 7?" is the strong one.

Style Girlfriend's Taylor Davies adds that you can recommend something she hasn't tried, like a song, a show or a place, and make her laugh in a way you're in on too. The Gentleman's Journal says to put the phone away, because texting or taking calls on a date says "I'm not interested."

She cares less about flashy gestures than whether you're consistent.

• Do what you say you'll do. If you say "I'll call you after work," call.
• If you need to reschedule, tell her early. Don't disappear and invent a tragic story about your crazy day.
• Remember little details. Social Self suggests making a note on your phone of things she says, like her pets' names or her favorite food, and bringing them up weeks later.
• Take care of yourself. A clean, trimmed look and a shirt that isn't crumpled are the easy version of effort.

Style Girlfriend suggests asking a follow-up question that invites her to say something about herself, like "How many siblings do you have?" then "Are you close with them?" Asking something that needs a little reflection invites her to open up, and it builds trust.

Be ready for the same questions yourself, and answer without sounding like a job interview.

She's watching how you talk about your ex, your sister, your female coworkers and the women you don't want to date. If you sound bitter, dismissive or entitled, she's gone. Social Self adds that the way you treat serving staff can show how you treat girlfriends.

"Women always want the same guys" is a bad line. "I've dated enough to know attraction is complicated, and I try to stay honest about what I bring to the table" is a better one.

Big feelings are fine. Unmanaged ones aren't. If something bothers you, say it directly. Instead of "Wow, must be nice to have all these male friends," try "I'll be honest, that situation makes me a little uncomfortable. Can we talk about it?"

Also don't make her your therapist. Social Self says emotionally aware people deal with their own issues without making her feel like a therapist. In our view, if you're still not over your ex, don't start calling someone new "different" and hoping that fixes it.

She won't build a relationship on your highlight reel. "If we stay together, I'm going to be amazing" is not enough. "I cook most nights, I handle my own life, and I communicate clearly" is something she can check.

If she wants to slow down, disagrees, or needs space, how you respond tells her everything. Don't negotiate like you're closing a deal and don't sulk. Say "Got it. I respect that."

Treat sex as something you pay attention to, not a performance review. Ask what she likes, notice what works, and adjust. "Slower here" and "more pressure" are useful information, and asking for it is a sign of confidence, not weakness.

The Gentleman's Journal says not to brag about how much you earn, and not to try to sleep with her on the first date. It also says compliments should be spontaneous and casual, early in the date: a passing "you look great" when you first see her, not a speech.

Experienced women are often clearer about what works for them. If she says she wants someone who communicates often, or who values alone time, take her at her word. Don't try to argue her into needing less.

The Modern Man says women have seen the "impress her" act from most men, sense it isn't the real personality, and lose respect. You don't need a better act. You need to be someone whose behavior matches what he says, which gets you further with any woman, not just one who has dated a lot.