How to Flirt with an Older Woman over Text

Easy ways to build your confidence when speaking to older women

Co-authored by Imad Jbara and Jessica Gibson

Last Updated: September 30, 2022 References

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.

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]
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Expert Source

Imad Jbara
Dating Coach
Expert Interview. 5 November 2019.} 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]
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- 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

Get her talking about herself.

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]
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- 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.

A selfie or even a nude could spice things up. 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]
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- 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.

4

Give her a specific compliment.

Be genuine and make her feel good about herself. 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]
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Expert Source

Imad Jbara
Dating Coach
Expert Interview. 5 November 2019.} Steer clear of vague or backhanded compliments like, "You look hot for a woman your age!"^{[6]
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- 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.”

5

Ask a flirty question.

Use a little cheekiness to get her to open up. Older women might be a little more guarded than younger women so flirt with her to break through her defenses. Text her something cute, fun, or naughty to see how she responds.^{[7]
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- Try something innocent like, “Why are you so cute?” or “How are you so perfect?”
- You could also try, “What would you do to me if I was there?” or “What are you wearing?”

6

Tease her a bit.

Keep it fun and playful to show her you feel comfortable. Try a little push-pull where you give her a teasing backhanded compliment. Use exaggeration to gently pick on her and make it clear that you're joking. Then, say something sweet to lighten the mood and show you're interested in her.^{[8]
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- Try sending, “That sounds like a fun night! I remember my first glass of wine” or “I can’t talk to you anymore, you’re just too much trouble for me.”

7

Add some sexy emojis.

Used properly, emojis can be an effective flirting tool. 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]
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- 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.

8

Avoid sending multiple messages in a row.

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]
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Expert Source

Imad Jbara
Dating Coach
Expert Interview. 5 November 2019.} 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]
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- 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.

Save sexting for a woman you really know well. 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]
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- 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.

Expert Q&A

Question

Is it okay to lie about your age in a relationship?

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
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.