How to Win a Stubborn Man's Heart

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Trying to win someone’s heart is never easy, but it becomes even more complicated when that person is stubborn. Fortunately, with a little time and patience, you can hopefully win over your potential lover’s heart and get him to see you for who you really are. Keep reading to learn how you can deal with a stubborn man and help him break down his walls to open up to you.

1

Let him come to you.

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    If you seem too eager about hanging out with him, it could be a turn off. You don’t have to cancel plans, but don’t rearrange your life for him. If he hits you up and you’re busy, reschedule for a different day. [1]
    • Make sure you’re not the only one initiating dates, too. Try to keep it about 50/50 to make sure he’s actually interested.
    • If he never approaches you to hang out at all, it could mean he’s just not interested. If you find that you’re constantly the one to initiate dates or hangout times, it might be time to move on.
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2

Open up to him.

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    Try to let him into your heart and share some intimate details about your life. You could tell him a story from your childhood, let him in on a secret, or tell him one of your most embarrassing moments. [2]
    • Hopefully, he’ll feel safe enough to open up to you, too.
    • Be vague about what you share, so he can ask you questions to get his undivided attention.
3

Be his friend.

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    If he’s not ready to call you his significant other yet, focus on being a really good friend. Eventually, you may just win him over enough to secure a romantic relationship with him. [3]
    • Think about what you’d want from a good friend: a shoulder to cry on, a listening ear, or someone to just have fun with.
    • Plus, showing him how caring you can be is a great way to show off your most empathetic and thoughtful qualities.
    • Reader Poll: We asked 196 wikiHow readers and 47% of them agreed that the characteristic they value most in a potential partner is an empathetic and caring nature . [Take Poll]
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4

Stay flirty.

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    Laugh at his jokes, touch him on the arm or the hand, and lean in a little closer than you normally would. [4] Keep it light and playful to remind him that you’re here to have fun, and you might just win him over. [5]
    • It might take a stubborn guy a little longer to flirt with you. This means you might have to lay it on a little thick at first!
    • If he flirts back, that’s a great sign that he’s becoming more interested in you.
Quiz

wikiHow Quiz: Does He Like Me?

Some guys can feel like a total mystery. How can you figure out if he likes you as just a friend—or if he wants something more? Take this quiz to find out!
1 of 15

When you two are in a room filled with other people, how often do you catch him staring at you?

5

Focus on your common interests.

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    Maybe you both read a lot, so you can spend time at a bookstore or the library. Or, maybe you two both like to surf, so you head out to the beach every Saturday. Try to do things that you both like together so he can see how compatible you are. [6]
    • It’s always good to try new things, too! If he’s interested in something you’ve never done before, give it a go. He’ll see you’re open to new interests (and how fun you are). [7]
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6

Make him laugh.

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    Tell a few jokes or get corny to make him chuckle. If he has a ton of fun with you, he’ll probably start to like you even more. [8]
    • This helps a ton if you two have a similar sense of humor.
7

Be silly in front of him.

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    Don’t worry too much about how you look or what you’re wearing—instead, make silly faces and dance like nobody’s watching. It shows that you’re cool and confident, even when you look a little goofy. [9]
    • Being silly around him will encourage him to let down his walls, too.
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8

Go on adventures together.

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    [10] Plan fun outings like going hiking or checking out a new museum. If he has a good time, he’ll associate the memory with you (and how awesome you are). [11]
    • You could try going on a picnic in the park, walking your animals together, taking a road trip to the beach, or even taking a weekend away together.
9

Live your own life.

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    Not only will this show him that you’re a well-rounded person who won’t be clingy, you’re also not rearranging your life for a man who is too stubborn to let you in. You can make him a priority in your life, but don’t sacrifice anything else for him. [12]
    • Plus, if you two don’t work out, you can slip effortlessly back into your life without changing much.
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Expert Q&A

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  • Question
    How do you deal with a stubborn man?
    Shana Tibi
    Certified Professional Matchmaker
    Shana Tibi is a Certified Professional Matchmaker, Date and Relationship Coach, and the Founder of Curated Connections, a matchmaking service for single professionals. Shana specializes in understanding core values and personal preferences to curate dates. She holds a BA in Peace Studies and Conflict Resolution from Prescott College and an MSW in Social Work from California State University, Hayward. She is an active member of the Global Love Institute where she earned her matchmaking certifications.
    Shana Tibi
    Certified Professional Matchmaker
    Expert Answer
    Try to figure out why he's stubborn. Do you understand his position? Do you understand his interest? Do you understand why he's feeling that way and having that experience? In answering those questions, you have to decide if his stubborn feelings and opinions are deal breakers for you.
    Thanks! We're glad this was helpful.
    Thank you for your feedback.
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    Not Helpful 2 Helpful 6
  • Question
    What is negotiable in a relationship?
    Shana Tibi
    Certified Professional Matchmaker
    Shana Tibi is a Certified Professional Matchmaker, Date and Relationship Coach, and the Founder of Curated Connections, a matchmaking service for single professionals. Shana specializes in understanding core values and personal preferences to curate dates. She holds a BA in Peace Studies and Conflict Resolution from Prescott College and an MSW in Social Work from California State University, Hayward. She is an active member of the Global Love Institute where she earned her matchmaking certifications.
    Shana Tibi
    Certified Professional Matchmaker
    Expert Answer
    That really depends on you and your partner's priorities and boundaries. For instance, a woman might be willing to negotiate moving to another country with her husband if he agrees to quit smoking.
    Thanks! We're glad this was helpful.
    Thank you for your feedback.
    If wikiHow has helped you, please consider a small contribution to support us in helping more readers like you. We’re committed to providing the world with free how-to resources, and even $1 helps us in our mission. Support wikiHow
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      Tips

      • If it’s been a few months and he’s still too stubborn to commit to you, it might be time to set your sights elsewhere.
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      • Show him that you have options and that you have a successful lifestyle.
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      • Stay focused on your goals, people are attracted to ambitious people.
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      References

      1. ↑ https://www.youtube.com/watch?t=219&v=PBotQygy7os&feature=youtu.be
      2. ↑ https://www.today.com/health/5-secrets-getting-man-open-I283741
      3. ↑ https://www.today.com/health/5-secrets-getting-man-open-I283741
      4. ↑ Shana Tibi. Certified Professional Matchmaker. Expert Interview. 19 October 2021.
      5. ↑ https://www.pride.com/lovesex/2019/9/20/12-ways-woo-guy-your-first-date#media-gallery-media-8
      6. ↑ Shana Tibi. Certified Professional Matchmaker. Expert Interview. 19 October 2021.
      7. ↑ https://www.cosmopolitan.com/uk/love-sex/sex/tips/g558/12-steps-make-him-love-you/?slide=2
      8. ↑ https://www.seventeen.com/love/dating-advice/a40429/things-that-make-guys-instantly-want-to-date-you/
      9. ↑ https://www.seventeen.com/love/dating-advice/a40429/things-that-make-guys-instantly-want-to-date-you/
      1. ↑ Shana Tibi. Certified Professional Matchmaker. Expert Interview. 19 October 2021.
      2. ↑ https://www.pride.com/lovesex/2019/9/20/12-ways-woo-guy-your-first-date#media-gallery-media-10
      3. ↑ https://www.youtube.com/watch?v=PBotQygy7os&t=135s

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