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How To Start A Conversation With A Woman Who Is Older In 7 Easy Ways

Older women have their stuff together and learning how to start a conversation with a woman like that can be daunting. But we break it down in seven easy steps.

Starting a conversation with a woman who’s older can seem intimidating. Women who are older are often more confident, more experienced, and less face it . . . harder to impress. They know who they are and what they want. They’re unlikely to give second chances after poor first impressions.

Figuring out how to start a conversation with a woman isn’t difficult once you know what they’re looking for. Doing it well does require some awareness. and will depend on where you're at. Each of the spots where we've had the best success meeting older women will require a slightly different approach for example.

Learning how to start a conversation with a woman who is older is a great way to learn successful conversation in general.

1) Learn the ways of the open-ended question, young Padawan

The key to how to start a conversation with an older woman and keep her interested is asking a question that will open up the dialogue. That means questions that elicit yes/no, good/bad answers are out. We call these “close-ended” questions because they pretty much close the door to further discussion.

Having a bit of confidence going in will definitely help and improve your chances. There are a few great books worth checking out that have really helped us out in that area.

Examples of closed-ended questions:

“How’s your drink?”

Possible answers: Good, bad, fine, great, I’ve had better.

Then she sits there staring at you and you have to come up with another one. Not good.

 “Are you enjoying yourself?”

Possible answers: Yes. No. Shrug.

Again, there’s no room for expansion and there’s no invitation for anything more than a basic response.

These are conversational dead-ends because they invite basic one-word answers. Unless you’ve happened upon someone particularly gregarious (or drunk) you’ll get a brief answer and that’ll be that.

Work on cultivating open-ended questions. These are questions that draw people out and invite them to engage on a more significant level. They convey the message that you’re interested in finding out more about them than superficial chit-chat yields. How to start a conversation with a woman is particularly important when it comes to a woman older than you.

She’s not going to give you the time of day if you come across as not having anything better than, “how’s it going?”

Example of open-ended question:

“Hi. Can I get you to tell me about that unusual-looking cocktail?”

This is a great question because she can go any one of a number of ways in response, and open up the conversation further. "Can I get you to tell me more about (fill in something you’ve observed here)?" is a generally great format because it’s not too specific but it’s also not obvious.

Learning how to talk to an older woman using open-ended questions will also improve your dialogue skills with friends, family, and colleagues.

Dating Apps Coaches Recommend to Meet Older Women

If you really want to get better at conversing with older women you just need to start meeting more of them. Most older women are meeting guys online now, many ONLY look online. There are a lot of apps out there but not many are great for meeting single older women.

Fortunately, our dating coaches have a ton of experience in this area. These are the best options right now that consistently work for regular guys:

SiteOur ExperienceOur RatingFree Trial Link
Best For Relationships
Experience Highlights
Experience Highlights
  • Easily the best option for long-term relationships
  • 75% of all online marriages start here
  • 70% of users meet their spouse within a year
  • In-depth signup and matching process
Try eHarmony
Best For Casual Fun
Experience Highlights
Experience Highlights
  • The best way to meet women for casual relationships
  • Best results for regular guys
  • Over 60 million active members
  • Not good for long-term relationships
Try AFF For Free
Decent For Younger Guys
Cougar Life Highlights
Cougar Life Highlights
  • Focused on younger men meeting older women
  • A mix of relationships and hookups
  • Growing
  • Not as popular as eHarmony of AFF
Try Cougar Life

2) Ask for input about something low-impact

Another means of how to start a conversation with a woman is to ask her for some type of input about the immediate environment. This is an open-ended question plus a gracious way to let her lead. “Low-impact” means nothing too personal or forward, like about your meddling ex who won’t let you keep the dog on weekends.

Example of asking for input about something low-impact:

  • “You look like you’re enjoying that drink immensely. Have any recommendations for a Whiskey-kinda-guy who’s trying to break out of a rut?”
  • “I can’t decide if I like this band or not. How’s it sitting with you?”
  • “What’s your investment level in this game?” (For sports-bar settings or bars with televisions behind them showing sports events).

Asking for input usually creates a sense of ease for the other person because everyone has opinions and they’re usually not tough to discuss.

3) Offer a thoughtful compliment

Everyone loves compliments. How to start a conversation with a woman is often as simple as noting something out loud to her that you’ve already mentioned to yourself (the appropriate ones).

Examples of thoughtful compliments:

  • Your hair is beautiful.
  • That’s a really unusual and eye-catching necklace.
  • Sexy shoes.

Simple compliments may seem, well, simple. But that’s part of their charm. Simple is not the same as simplistic. And in a social world where everyone is trying hard to be clever, a simple and genuine compliment might very well be a breath of fresh air to any woman.

4) Just say “hi”

Okay, yes, when figuring out how to start a conversation with a woman you’ll have to have a follow-up to a greeting. But like a thoughtful compliment, a simple greeting indicates authenticity, openness, and a distinct lack of artifice.

Women who are older are particularly good at sniffing out BS. The fancier your approach, the less likely they are to respond.

5) Send her a drink

This is a classic and there’s a reason for it. When you’re working out how to start a conversation with a woman, it never hurts to show some bold masculine initiative right up front.

Sending a drink to a woman is assertive and confident without being aggressive or pushy. And it's a great way to attract women without even talking. Utilize your server or the bartender . . . make sure they get her what she’s drinking, not something you pick out for her.

6) Sit down next to her

If she’s by herself, this is easy.

If she’s with a friend, it’s a little trickier. You run the risk of intruding on a social interaction that she’s into already. However, some of the same rules apply.

Mainly, be present without being intrusive. If a woman you want to start a conversation with is sitting at a bar by herself or with a friend, sit down on the other side of her and be patient. Do your own thing.

At some point, if she’s curious about you, she’ll engage you when there’s a lull in her other conversation. Guaranteed, she’s aware of you the minute you sit down.

7) If you want to learn to how start a conversation with a woman successfully every time — Learn to listen

Figuring out how to start a conversation with a woman is actually the easy part. There are a million scenarios that might throw you into each other’s conversational orbit. The real question is, what do you do once you get there? How are you going to keep it going? All of these 7 ways of how to start a conversation with a woman are also great ways to keep a conversation going.

  • Get your open-ended questions going
  • Use genuine compliments, and sparingly
  • Ask her for her opinion
  • Offer to grab her another beverage
  • Just say “hi”
  • Really listen

Starting a conversation happens again and again, technically, in the course of an exchange. Each moment is an opportunity to expand the dialogue or contract it. Using these tips on how to start a conversation with a woman will help you keep conversations going, as well. And in the end she might even tell you "hit me up".

A note about “don’ts” when it comes to starting the conversation

If there’s one golden-, sacred rule regarding how to start a conversation with a woman who is older, it’s this:

Thou shalt not blather about thyself. Nor shalt thou blather about her.

Women who are older are looking for a balance, and they know how to engage and be engaged. If you fawn over her, you’ll turn her off in a hot second. She doesn’t need or want a fan club. If you fawn over yourself, your game will be dead in the water. She doesn’t need or want to be someone else’s fan club. She’s looking for an interaction of equals.

Three lesser rules that will stand you in good stead when learning how to start a conversation with a woman who’s caught your eye are:

  • Don’t brag or look for openings to let her know how awesome you are. Don’t slip in accomplishment references.

If the course of the conversation naturally presents an opportunity for you to mention your slalom times at the Olympic trials, sure . . . Go for it. Otherwise, keep your stats in your pants.

  • Don’t leer.

If she wasn’t hot or if she didn’t have a certain vibe, you wouldn’t be trying to figure out how to start a conversation with her in the first place. Women appreciate being appreciated. They don’t appreciate being gawked at. Keep your eyes up.

  • Don’t overstay your welcome.

Look . . . Sometimes it’s just not going to go any further. Be gracious, be mature, and be gone.

Learning how to start a conversation with a woman who is older than you is about being conscientious. That means being aware of what she’s doing and saying, as well as what you’re doing and saying. You can also talk dirty to her and turn her on.

It’s worth your time to sit down and think through some of the nonverbal messages you intentionally or unintentionally may be conveying. Ask yourself if those messages are really communicating what you mean to relay. Chances are, you can refine your game quite a bit.

This will help you start a conversation with a woman and keep it going in a great direction.


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