How to Win a Stubborn Man's Heart

Co-authored by Shana Tibi and Hannah Madden

Last Updated: December 12, 2024 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.

Download Article

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]
X
Research source}
- 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.

Download Article

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]
X
Research source}
- 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.

Download Article

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]
X
Research source}
- 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 220 wikiHow readers and 46% of them agreed that the characteristic they value most in a potential partner is an empathetic and caring nature. [Take Poll]

4

Stay flirty.

Download Article

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]
X
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]
X
Research source}
- 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?

Constantly! I swear, he’s always looking right back at me.

I’ve noticed him staring a few times, yeah.

I think I’ve caught him staring once or twice.

Nope, I’ve never noticed that.

5

Focus on your common interests.

Download Article

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]
X
Expert Source

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]
  X
  Research source}

6

Make him laugh.

Download Article

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]
X
Research source}
- This helps a ton if you two have a similar sense of humor.

7

Be silly in front of him.

Download Article

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]
X
Research source}
- Being silly around him will encourage him to let down his walls, too.

8

Go on adventures together.

Download Article

Show him just how fun it would be if you two were dating.^{[10]
X
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]
X
Research source}
- 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.

Download Article

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]
X
Research source}
- Plus, if you two don’t work out, you can slip effortlessly back into your life without changing much.

Expert Q&A

Search

Add New Question

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.
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
Yes No

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
Yes No

Not Helpful 0 Helpful 2

Ask a Question

200 characters left

Include your email address to get a message when this question is answered.

Submit

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.

Thanks
Helpful 0 Not Helpful 0
Show him that you have options and that you have a successful lifestyle.

Thanks
Helpful 0 Not Helpful 0
Stay focused on your goals, people are attracted to ambitious people.

Thanks
Helpful 0 Not Helpful 0