How to Text an Older Guy: 9 Expert Tips to Impress & Interest Him

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The best ways to interest and engage an older guy over text
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Texting a new guy is always fun. If you're getting to know an older guy, you might have some unique questions about how to impress him or show off your maturity. Luckily, there's a lot you can do to intrigue an older guy when you text while also remaining true to yourself.

Things You Should Know

  • Remember to be yourself so the guy you're texting ends up liking you for you.
  • Bring up current events you're interested in as a conversation topic.
  • Don't be freaked out if he doesn't text back right away or never uses emojis, as different generations text differently.
1

Be yourself first and foremost.

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  1. You don't have to change yourself to make an older guy like you. Be open about who you are. Tell him what you like to do for fun, let your sense of humor shine, and try to relax. It may be tempting to hide your interests or change how you communicate for an older man, but it's not a good idea in the long run. Be yourself so that he likes you for you. [1]
    • If you're going to a club with your friends, don't hide it because you think it makes you sound less mature. Say something like, "I've been dancing with my friends tonight. Do you like dancing?" It's best just to be upfront and honest. [2]
    • If you feel like you have to change yourself to keep his attention, he may not be a good match for you. The person you like should make you feel more comfortable being yourself, not the other way around. [3]
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2

Text him about your career and accomplishments.

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  1. An older guy is likely to be more secure in his accomplishments, so he'll be impressed by yours. If your artwork was published in a magazine recently or you just got a job promotion, text him about it. Be open about your goals, and don't be shy in revealing how you plan to reach them. [4]
    • If he asks what you're up to at work, be open about the specifics. Text him something like, "I've been organizing an event the past few weeks. I'm responsible for hiring the caterers and booking the musical guests!"
3

Talk about current events.

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  1. If there's a lull in the text conversation, bring up what's happening in the news. Share your opinion about current issues in politics and pop culture, and text him questions about his point of view. Though your opinions and even the way you consume news may be different due to your age difference, approach the conversation like equals. [5]
    • If you're unsure about how to bring up the subject, reference an article you recently read or a book that helped you learn about the subject.
    • Just because he's older doesn't mean he knows more about current events than you. Try not to be intimidated, and don't let him talk down to you. A relationship has got to be founded upon mutual respect, no matter the age difference.
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4

Ask him questions about his life or experiences.

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  1. Take an interest in his life by asking him questions. Maybe he traveled the world for a few years before settling down in the city you both live in. Ask him about his favorite place to visit or his favorite travel story. Text him questions about his career and hobbies, too. You might even learn some new things from his varied experiences. Just make sure he's open to learning from you, too. [6]
    • Maybe he lived in New York City for a few years in his twenties. Ask him something like, "What was it like living in New York City? Do you ever miss it?"
    • If he's been painting in his spare time for ten years, text him, "What's your favorite medium to paint with? Has it changed over the years?"
5

Send him a funny video.

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  1. A fun way to break the ice and even flirt a little is to show off your comedic chops. [7] Send a funny YouTube video that made you think of him or even a GIF from a TV show you both like. Laughing together (even over text) is a great way to establish common ground with an older guy. It's also a great opportunity to show off your wit. [8]
    • Maybe you're both huge fans of the show The Office. Send him a clip of your favorite scene with the caption, "Can't stop laughing at this."
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6

Use emojis to your advantage.

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  1. If you're joking around or using sarcasm, throw in a smiley face to make sure he knows you're just kidding around. Add a red heart or a heart eyes emoji when you send something flirty. [9] Don't use them in every text you send, though. An older guy probably won't use as many emojis, and he may be overwhelmed or turned off by too many heart eyes and smiley faces. [10]
    • Don't worry if your older guy never uses emojis. Different generations use texting in different ways. Sometimes, that results in older guys using fewer emojis (or none at all).
7

Make time for your hobbies and interests.

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  1. This can come off as a little clingy. Instead, fill up your time with your hobbies and passions so that you only text him when you've got something new and interesting to say. Hang out with your friends, go on interesting day trips, and stay focused on your hobbies like hiking and playing music. [11] Older guys are more likely to be attracted to strong, independent people. [12]
    • It can be tempting to neglect your hobbies and responsibilities when you really like someone, especially a successful older guy. Stay focused on yourself so that you remember how awesome and successful you are on your own.
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8

Avoid texting too much.

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  1. Different generations use texting a little differently and may not be as up for hours of chatting and banter. Use texting to catch up and make plans, but rely on in-person conversations to really get to know each other. Don't fret about response times, either. Text in moderation (1 text a day or a few throughout the week) and prioritize your time together off the phone. [13]
    • Avoid double-texting when you haven't heard from him in a few hours. He may be at work or busy with other plans.
9

Stay safe when you text.

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  1. It's unfortunate, but some older guys may be interested in a younger person for the wrong reasons. If they frequently talk down to you when you text or pressure you to send explicit texts, those are red flags. Don't give away too many personal details about your life when you first start texting. Avoid sexting or sharing an intimate photo of yourself with someone you don't completely trust or know well.
    • Trust your intuition and wait until you really feel comfortable around him to share more personal things.
    • Walk away if they seem controlling, manipulative, or condescending. You deserve to be treated like an equal.
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Improve Your Texting Game with this Expert Series

Not sure how to text a guy to get his attention and keep him interested? We’ve put together this series of expert articles to help you text easily and confidently.
1
Text a Guy on a Dating App
2
How Often Should a Guy Text You in the Beginning?
3
Text a Guy After the First Date
4
How to Drop Hints to a Guy You Like & Get Him to Ask You Out
5
Get Attention from a Guy over Text
6
How to Ask a Guy to Hook Up over Text + Flirting Tips

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      References

      1. ↑ https://www.amherst.edu/campuslife/health-safety-wellness/counseling/self_care/healthy_relationships/10_tips_for_health_realtionships
      2. ↑ https://stylecaster.com/dating-older-men/
      3. ↑ https://www.psychologytoday.com/us/blog/constructive-wallowing/202011/how-be-yourself-in-relationship
      4. ↑ https://www.vogue.com/article/the-mature-allure-dissecting-the-attraction-of-the-older-man-breathless-karley-sciortino-slutever
      5. ↑ https://www.americanpressinstitute.org/publications/reports/survey-research/social-demographic-differences-news-habits-attitudes/
      6. ↑ https://stylecaster.com/dating-older-men/
      7. ↑ https://www.psychologytoday.com/us/basics/flirting
      8. ↑ https://theconversation.com/how-humour-can-change-your-relationship-106402
      9. ↑ https://www.nytimes.com/2019/03/19/magazine/how-to-use-emojis.html
      1. ↑ https://www.thecut.com/2018/01/the-worst-part-of-dating-an-older-guy-is-his-texting-habits.html
      2. ↑ https://www.helpguide.org/articles/relationships-communication/relationship-help.htm
      3. ↑ https://www.vogue.com/article/the-mature-allure-dissecting-the-attraction-of-the-older-man-breathless-karley-sciortino-slutever
      4. ↑ https://www.thecut.com/2018/01/the-worst-part-of-dating-an-older-guy-is-his-texting-habits.html
      5. ↑ Joshua Pompey. Relationship Expert. Expert Interview. 27 November 2019.

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