How to Win a Stubborn Man's Heart

Co-authored by Shana Tibi and Hannah Madden

Last Updated: October 28, 2021 References

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.

Don’t make yourself available 24/7. 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]
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- 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.

2

Open up to him.

If he sees you opening up, he’s more likely to do it too. 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]
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- Hopefully, he’ll feel safe enough to open up to you, too.

3

Be his friend.

Uplift him, support him, and just be there for him. 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]
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- 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.

4

Stay flirty.

Remind him that you think he’s cute, funny, and sexy. Laugh at his jokes, touch him on the arm or the hand, and lean in a little closer than you normally would.^{[4]
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Expert Source

Shana Tibi
Certified Professional Matchmaker
Expert Interview. 19 October 2021.} Keep it light and playful to remind him that you’re here to have fun, and you might just win him over.^{[5]
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- 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.

5

Focus on your common interests.

What do you two like to do together? 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]
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Shana Tibi
Certified Professional Matchmaker
Expert Interview. 19 October 2021.}
- 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.

Show off your sense of humor whenever you’re together. 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]
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- This helps a ton if you two have a similar sense of humor.

7

Be silly in front of him.

Let him see how comfortable you are around him. 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]
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- Being silly around him will encourage him to let down his walls, too.

8

Go on adventures together.

Show him just how fun it would be if you two were dating.^{[10]
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Expert Source

Shana Tibi
Certified Professional Matchmaker
Expert Interview. 19 October 2021.} 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]
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- 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.

Keep up with your own friends and hobbies. 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]
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- Plus, if you two don’t work out, you can slip effortlessly back into your life without changing much.

Expert Q&A

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.
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.