PDF download Download Article
Easy ways to build your confidence when speaking to older women
PDF download Download Article

Flirting with an older woman may seem confusing or intimidating, but it really isn’t! It’s actually super simple and really fun. The key is to just know your audience. To help you nail the conversation, we’ve put together a list of helpful suggestions and ideas you can use to successfully flirt with an older woman over text.

1

Open with a thoughtful or playful message.

PDF download Download Article
  1. Set a fun and flirty tone right from the start. Most women regardless of age dislike a boring opener like “Hey” or “Hi.” Get creative and send her something that shows her you were thinking of her.[1] If you have a history or you have any inside jokes, text her something that’s specific and special to your relationship with her. It’ll make her feel special and warm her up for some fun flirting.[2]
    • For instance, you could try, “I was just driving around listening to Edith Piaf and thinking of you.”
    • You could also try, “Have you ever dated someone more than 10 years younger than you?"
    • Use straightforward textspeak that she's more likely to understand. If she hasn't been keeping up with popular text abbreviations, she might not get a message like "WYD." Go ahead and text her the full, "What are you doing?" just to play it safe.
  2. Advertisement
2

Get her talking about herself.

PDF download Download Article
  1. Ask questions to keep the conversation going. An older woman probably has a lot of rich life experiences that you can ask about. This is a fantastic way to get to know her. You might ask open-ended questions about places she's traveled, unique experiences she's had, or jobs she's had in the past.[3]
    • Try something like, “What was your first job?” or “What is your favorite country that you’ve ever visited?”
    • You could also try, “I’ve never gone skydiving. I’m too chicken! Have you? Are you daring like that?”
    • Once you get the ball rolling, it’ll be easier to flirt with her. Plus, you may be able to use some of the details she tells you. For instance, if she talks about how much she loves chocolate, you could say, “Have you ever tried chocolate with red pepper? Spicy and sweet, just like you!”
3

Send a photo of yourself if you’re feeling brave.

PDF download Download Article
  1. Just because she's older than you doesn't mean she won't be interested in getting hot photos from you. Text her a good-looking pic of your smiling face and she might send you one in return. If you feel really comfortable texting her or you’ve been texting each other for a while, take a chance and send her a more risque shot of yourself![4]
    • Try adding a caption like, “Do you like what you see?” or “How do I look?”
    • If you’ve just started texting her, you may want to hold off on a fully nude photo until you’ve gotten to know each other and she seems open to it.
  2. Advertisement
4

Give her a specific compliment.

PDF download Download Article
  1. Talk about something that she does really well and give her props for it. If you want to compliment her appearance or something physical about her, go with something specific so it feels more genuine.[5] Steer clear of vague or backhanded compliments like, "You look hot for a woman your age!"[6]
    • For instance, you could text, “You’ve got incredible hair. It’s always salon quality” or “You’re so fit and strong! Your biceps are insane.”
    • You could also stick to her professional accomplishments and say, “I bet you’re an amazing lawyer. I wouldn’t want you suing me” or “No wonder you’re a great real estate agent. You’re so charming.”
7

Add some sexy emojis.

PDF download Download Article
  1. Pepper in some smiley face and heart emojis to keep the conversation friendly, but don’t be afraid to spice things up. An eggplant or a devil face emoji can add an extra layer of flirtation to your texts. Emojis are also great since they're more straightforward than popular textspeak, which she might not be familiar with.[9]
    • For instance, if she asks something like, “What are you having for lunch?” You could say, “I wish I was having you” or “I’d rather be with you” and add a devil face emoji or a smiley face with the tongue sticking out.
  2. Advertisement
8

Avoid sending multiple messages in a row.

PDF download Download Article
  1. Blowing up her phone could make you seem desperate. An older woman probably has experience with a needy partner and you don't want to seem thirsty![10] It's fine to double-text occasionally, but don't send 3 messages back to back. Wait for her responses—after all, flirting is a two-way street.[11]
    • Keep your messages short and sweet so you can save longer conversations for when you're face-to-face.
    • If you forgot to mention something, you can always text it later, after she’s responded.
    • Avoid sending messages like “hello?” or “you there?” or “?” if she takes some time to respond. It could make you seem pushy.
9

Steer clear of filthy language.

PDF download Download Article
  1. Some women, especially ones you just met, might be turned off by suggestive language. However, if you've been flirting with a woman you know well and think she'd be receptive, go for it. The key is to see how she responds to your messages. Use them as a guide to either keep sexting or clean it up.[12]
    • For instance, if she quickly texts back with a flirty, sexy message, she's probably open to more sexting. If a lot of time passes before she responds or she starts talking about something else, she's probably uncomfortable with it.
  2. Advertisement

Expert Q&A

Search
Add New Question
  • Question
    Is it okay to lie about your age in a relationship?
    Imad Jbara
    Imad Jbara
    Dating Coach
    Imad Jbara is a Dating Coach for NYC Wingwoman LLC, a relationship coaching service based in New York City. 'NYC Wingwoman' offers matchmaking, wingwoman services, 1-on-1 Coaching, and intensive weekend bootcamps. Imad services 100+ clients, men and women, to improve their dating lives through authentic communication skills. He has a BA in Psychology from the University of Massachusetts Dartmouth.
    Imad Jbara
    Dating Coach
    Expert Answer
    Lying about your age isn't a great idea. You're basically starting the foundation of your relationship on a lie, which is never good.
  • Question
    What should I know about dating an older woman?
    Imad Jbara
    Imad Jbara
    Dating Coach
    Imad Jbara is a Dating Coach for NYC Wingwoman LLC, a relationship coaching service based in New York City. 'NYC Wingwoman' offers matchmaking, wingwoman services, 1-on-1 Coaching, and intensive weekend bootcamps. Imad services 100+ clients, men and women, to improve their dating lives through authentic communication skills. He has a BA in Psychology from the University of Massachusetts Dartmouth.
    Imad Jbara
    Dating Coach
    Expert Answer
    Don't tell her age, if you can. Definitely don't lie—just try to avoid the question with a clever comeback, like "Not old enough to be an awesome guy." Keeping your age a secret allows her to get to know you for who you are.
Ask a Question
200 characters left
Include your email address to get a message when this question is answered.
Submit
Advertisement

Video

Tips

  • If she seems slow to respond, she may just be busy. Give her some time and she may start engaging with you more.
Submit a Tip
All tip submissions are carefully reviewed before being published
Name
Please provide your name and last initial
Thanks for submitting a tip for review!
Advertisement

You Might Also Like

Rizz LinesThe Ultimate Collection of Funny, Cheesy, & Romantic Rizz Lines
21 Questions Game Freaky21 Questions Game: Spicy & Freaky Questions to Get to Know Your Crush
Flirty Compliments for a Girl100+ Flirty Things to Say to a Girl & Boost Her Self-Esteem
Signs a Man Is Sexually Attracted to You20+ Signs a Guy is Attracted to You
Flirty Jokes to Make Her Laugh140 Flirty Jokes & Pick-Up Lines to Make Her Laugh
Seduce a ManSeduce a Man
Seduce a WomanSeduce a Woman
Flirty Good Morning Texts for Him70+ Sweet, Playful & Steamy Good Morning Texts To Send Your Man
Be Smooth with the Ladies3 Ways to Be Smooth and Rizz Up a Girl
Seduce an Older WomanSeduce an Older Woman
Turn Ons for MenWhat Are the Biggest Turn-Ons for Guys?
Read Women's Body Language for FlirtingReading Women’s Body Language: Signs & Signals That She’s Flirting
FlirtFlirt
Talk to a GirlTalk to a Girl
Advertisement

About This Article

Imad Jbara
Co-authored by:
Dating Coach
This article was co-authored by Imad Jbara and by wikiHow staff writer, Jessica Gibson. Imad Jbara is a Dating Coach for NYC Wingwoman LLC, a relationship coaching service based in New York City. 'NYC Wingwoman' offers matchmaking, wingwoman services, 1-on-1 Coaching, and intensive weekend bootcamps. Imad services 100+ clients, men and women, to improve their dating lives through authentic communication skills. He has a BA in Psychology from the University of Massachusetts Dartmouth. This article has been viewed 433,643 times.
How helpful is this?
Co-authors: 6
Updated: January 12, 2024
Views: 433,643
Categories: Flirting | Texting
Thanks to all authors for creating a page that has been read 433,643 times.

Is this article up to date?

Advertisement