150+ Text Messages for Your Ex Boyfriend: Heartfelt, Friendly & Closure-Focused Messages That Actually Work

Sarah stared at her phone for twenty minutes, typing and deleting the same message to her ex boyfriend. Sound familiar? According to a Pew Research study, 88% of people have difficulty navigating digital communication after breakups, often sending messages they later regret.

Photo by Felicity Tai on Pexels

Sarah stared at her phone for twenty minutes, typing and deleting the same message to her ex boyfriend. Sound familiar? According to a Pew Research study, 88% of people have difficulty navigating digital communication after breakups, often sending messages they later regret.

The truth is, most people get post-breakup texting completely wrong. They either come across as desperate, angry, or confusing—none of which helps anyone heal or move forward.

I've compiled over 150 text messages for your ex boyfriend, organized by situation and intent. Whether you're seeking closure, maintaining friendship, or simply need to handle practical matters, you'll find messages that preserve your dignity while achieving your communication goals.

Friendly Check-In Messages After Some Time Apart

Sometimes you genuinely want to know how your ex is doing without any romantic agenda.

Friendly check-in messages work best 3-6 months post-breakup when both parties have processed the relationship ending and can communicate without heavy emotional baggage.

• "Hey [Name], hope you're doing well. Saw your promotion post on LinkedIn - congratulations! You always worked so hard for that."
• "Hi! Just wanted to check in and see how you're settling into the new apartment. Hope the move went smoothly."
• "Hey there, been thinking about you lately (in a good way). How's the new job treating you?"
• "Hi [Name], hope you're well. Heard through [mutual friend] that you got into grad school - that's amazing! You deserve it."
• "Hey, just saw that photo of your hiking trip. Looks incredible! Hope you're doing great."
• "Hi there, hope life's treating you kindly. How's your family doing?"
• "Hey [Name], randomly thought of that joke you used to tell. Hope you're still making people laugh wherever you are."
• "Hi! Hope you're doing well. How's [pet's name] adjusting to the new place?"
• "Hey, hope you're good. Saw your band's new song on Spotify - really great stuff as always."
• "Hi [Name], hope you're well. How did that presentation you were nervous about go?"

Tip: Consider sending a small care package or flowers if the conversation goes well and you want to show genuine friendship.

Closure and Understanding Messages

When you need answers or want to express final thoughts for your own peace of mind.

Closure messages should focus on your own healing journey rather than attempting to restart the relationship or assign blame for what went wrong.

• "Hi [Name], I've been doing a lot of thinking lately. I wanted to thank you for the good times we shared and wish you genuine happiness."
• "Hey, I know we didn't end on the best terms, but I wanted you to know I don't hold any grudges. I hope you're doing well."
• "Hi [Name], I've been working on myself and wanted to say I understand why things didn't work out. No hard feelings."
• "Hey there, I realize I never properly thanked you for [specific positive thing]. It meant more than you knew."
• "Hi [Name], I've learned a lot about myself since we broke up. I wanted to say I'm grateful for what we had, even though it didn't last."
• "Hey, I know this might seem random, but I wanted closure for myself. I wish things had been different, but I respect where we are now."
• "Hi [Name], I've been seeing a therapist and working through some things. I wanted you to know I understand my part in our problems."
• "Hey there, I hope you're happy. That's all I ever wanted for you, even if I didn't show it well sometimes."
• "Hi [Name], I know we can't go back, but I wanted you to know our relationship taught me what I want in life. Thank you for that."
• "Hey, I've found peace with how things ended. I hope you have too. Wishing you all the best."

Apology Messages That Show Genuine Growth

Taking accountability requires courage and specificity, not just generic "I'm sorry" statements.

Effective apology messages to ex boyfriends demonstrate specific behavioral changes and personal insights without expecting forgiveness or reconciliation in return.

• "Hi [Name], I've been reflecting on my behavior during our relationship. I realize I was controlling about your friends, and that wasn't fair. I'm working on this in therapy."
• "Hey, I owe you an apology. I know I shut down during arguments instead of communicating. I'm learning better conflict resolution skills now."
• "Hi [Name], I want to apologize for how I handled our breakup. My anger came from hurt, but you didn't deserve that treatment."
• "Hey there, I've realized I projected my insecurities onto you, especially about [specific situation]. That wasn't your burden to carry. I'm sorry."
• "Hi [Name], I apologize for not respecting your boundaries when you asked for space. I understand now why that was important."
• "Hey, I want to acknowledge that I wasn't emotionally available during [specific time period]. You deserved better support from me."
• "Hi [Name], I'm sorry for making you feel like you had to choose between me and your goals. I should have been more supportive."
• "Hey there, I realize I never properly apologized for [specific incident]. My pride got in the way, but you deserved better."
• "Hi [Name], I've learned that my jealousy issues stemmed from my own fears. I'm sorry you had to deal with that insecurity."
• "Hey, I want to apologize for not listening when you tried to tell me what you needed. I hear you now, even if it's too late."

Tip: Consider accompanying your apology with a meaningful book on personal growth to show you're serious about change.

Birthday and Special Occasion Messages

Acknowledging important dates requires careful consideration of boundaries and timing.

Birthday messages to ex boyfriends should be brief, genuine, and free from hidden agendas or attempts to rekindle romantic feelings.

• "Happy birthday, [Name]! Hope you have a wonderful day surrounded by people who care about you."
• "Hey, happy birthday! Hope this new year brings you everything you're hoping for."
• "Happy birthday, [Name]! Hope you're celebrating in style. You deserve all the good things."
• "Hey there, happy birthday! Hope your day is as amazing as you are."
• "Happy birthday! Hope you get to do something you really love today."
• "Hey [Name], happy birthday! Hope this year is your best one yet."
• "Happy birthday! Hope you're surrounded by laughter and good vibes today."
• "Hey, happy birthday! Hope you get all your favorite cake and none of the calories. 😊"
• "Happy birthday, [Name]! Hope your special day is everything you want it to be."
• "Hey there, happy birthday! Hope you're making some great memories today."
• "Congratulations on your graduation! You worked incredibly hard for this achievement. So proud of you."
• "Hey, heard about your promotion! You absolutely earned it. Congratulations!"
• "Hi [Name], saw the news about your [achievement]. You should be really proud - that's incredible!"

Messages During Difficult Times or Emergencies

Offering support during crises requires balancing compassion with appropriate boundaries.

Support messages during emergencies should prioritize their wellbeing over your desire to reconnect and respect their support system boundaries.

• "Hi [Name], heard about your dad. I'm so sorry for your loss. If you need anything at all, please don't hesitate to reach out."
• "Hey, [mutual friend] told me about the accident. I hope you're okay and recovering well. Sending healing thoughts your way."
• "Hi [Name], I know we don't talk much anymore, but I heard about your mom's diagnosis. I'm here if you need someone to listen."
• "Hey there, heard you're going through a tough time at work. I know how much that job meant to you. Hope things improve soon."
• "Hi [Name], saw the news about the fire at your apartment building. I hope you and [pet's name] are safe and have somewhere to stay."
• "Hey, heard about your surgery. I know you're in good hands, but I wanted you to know I'm thinking of you."
• "Hi [Name], I know this is a difficult time with your family situation. You don't have to respond, but I wanted you to know I care."
• "Hey there, heard through [mutual friend] that you're dealing with some health issues. Sending you strength and positive energy."
• "Hi [Name], I know we're not together anymore, but I still care about your wellbeing. Hope you're getting the support you need right now."
• "Hey, heard about what happened. I won't pretend to know what you're going through, but I'm here if you need a friend."

Co-Parenting and Shared Responsibility Messages

When children or shared obligations require ongoing communication, professionalism is key.

Co-parenting messages should remain business-like and child-focused, avoiding personal relationship topics that could create unnecessary tension or confusion.

• "Hi [Name], can we discuss [child's name]'s schedule for next week? I have a work commitment on Thursday evening."
• "Hey, [child's name] mentioned wanting to join soccer. Can we talk about logistics and costs this weekend?"
• "Hi [Name], [child's name] has been asking about the family vacation plans. Should we coordinate our summer schedules?"
• "Hey there, [child's name]'s teacher wants to meet with both of us about their reading progress. Are you available Tuesday afternoon?"
• "Hi [Name], [child's name] left their backpack at your place. Can I pick it up tomorrow before school?"
• "Hey, [child's name] has a doctor's appointment next Friday at 3 PM. Can you take them, or should I rearrange my schedule?"
• "Hi [Name], we need to discuss [child's name]'s birthday party plans. They want to invite friends from both schools."
• "Hey there, [child's name] mentioned they want to learn guitar. Should we split the lesson costs?"
• "Hi [Name], [child's name]'s school is having a parent conference. Can we coordinate who attends which sessions?"
• "Hey, [child's name] needs new winter clothes. Should we go shopping together or divide the list?"

Tip: Consider using a co-parenting app or shared calendar to minimize direct communication while staying organized.

Messages When You Want to Reconnect Romantically

Expressing renewed interest requires honesty about what's changed since the breakup.

Reconnection messages should demonstrate specific changes in yourself or circumstances rather than simply expressing that you miss the relationship.

• "Hi [Name], I know this might surprise you, but I've been doing a lot of work on myself since we broke up. I'd love to talk if you're open to it."
• "Hey there, I've learned so much about what I want in a relationship. I realize now what I took for granted with you. Can we talk?"
• "Hi [Name], I know I hurt you, and I've spent months understanding why. I'm not the same person who made those mistakes. Would you be willing to hear me out?"
• "Hey, I've been in therapy working on the issues that caused problems between us. I understand if you're not interested, but I'd love a chance to show you how I've grown."
• "Hi [Name], I know we said we needed space, and that time has been valuable. I've realized what really matters to me. Can we meet for coffee?"
• "Hey there, I've been thinking about us a lot lately. I know I wasn't ready before, but I am now. Would you be open to talking?"
• "Hi [Name], I understand if you've moved on, but I had to tell you - I still have feelings for you. I've changed in ways I think you'd appreciate."
• "Hey, I know this is unexpected, but I can't stop thinking about what we had. I've worked on myself and wonder if we could try again."
• "Hi [Name], I've realized that what we had was special, and I let my fears ruin it. I'm not afraid anymore. Would you consider giving us another chance?"
• "Hey there, I know I said I needed to focus on my career, but I've learned that success means nothing without someone to share it with. I miss you."

Messages for Returning Personal Items or Practical Matters

Logistics require straightforward communication without emotional complications.

Practical messages about belongings or logistics should be straightforward and business-like, avoiding emotional language that could complicate simple arrangements.

• "Hi [Name], I have some of your books and that blue sweater. When would be a good time for you to pick them up?"
• "Hey, I found your charger and those sunglasses you were looking for. Should I drop them off or leave them with [mutual friend]?"
• "Hi [Name], I still have your Netflix password saved. Should I log out, or do you want to change it?"
• "Hey there, I need to get my winter coat and laptop from your place. Are you free this weekend for a quick pickup?"
• "Hi [Name], we need to figure out what to do about the joint gym membership. Should we cancel or transfer it?"
• "Hey, I have your mail here from the past few weeks. Want me to forward it to your new address?"
• "Hi [Name], I found that ring your grandmother gave you. I know it's important to you - when can I get it back to you?"
• "Hey there, we need to close the joint bank account. Are you available to go to the bank together this week?"
• "Hi [Name], I have your spare car key. Should I mail it to you or leave it somewhere convenient?"
• "Hey, I need to get my tools from your garage. Would Saturday morning work for you?"

Messages When You're Ready to Be Friends

Transitioning to friendship requires clear intentions and realistic expectations.

Friendship messages work best when both parties have genuinely moved past romantic feelings and can interact without hidden agendas or expectations.

• "Hi [Name], I've been thinking that we made better friends than we did partners. Would you be interested in trying that?"
• "Hey there, I miss having you in my life as a friend. I know it might take time, but I'd love to rebuild that connection."
• "Hi [Name], I realize what I miss most is your friendship. No romantic feelings, just genuine care for you as a person. Think we could try being friends?"
• "Hey, I know it might seem weird, but I think we could have a great friendship if we're both truly over the romantic stuff. What do you think?"
• "Hi [Name], I've moved on romantically and hope you have too. I'd love to have you back in my life as a friend if you're open to it."
• "Hey there, I miss our conversations and your perspective on things. Think we could grab coffee as friends sometime?"
• "Hi [Name], I know we tried the relationship thing and it didn't work, but I think we could be amazing friends. Interested?"
• "Hey, I've realized that losing you as a friend was the hardest part of our breakup. Would you be willing to try rebuilding that?"
• "Hi [Name], I know it takes time, but I hope someday we can be friends again. You're too good a person to lose completely."
• "Hey there, I miss having someone who gets my weird sense of humor. Think we could be friends without the complicated stuff?"

Custom Message Creation Tips

Before hitting send, ask yourself these crucial questions. What's my real motivation for reaching out? Am I seeking closure, friendship, or secretly hoping to get back together?

Timing matters more than perfect words. According to relationship experts, waiting at least 30 days after a breakup allows emotions to settle and perspectives to clear.

Your tone should match your true intentions. If you want friendship, sound friendly but not flirtatious. If you're seeking closure, be sincere but not desperate.

Set boundaries for yourself before sending any message. Decide how many follow-up texts you'll send (hint: usually just one), and stick to that limit regardless of their response.

Watch for red flags in your own behavior. If you're drunk, extremely emotional, or hoping to make them jealous, step away from your phone.

Prepare for any response—or no response at all. They might be happy to hear from you, completely uninterested, or somewhere in between. Your peace of mind shouldn't depend on their reaction.

Tip: Consider investing in a journal or therapy sessions to work through your feelings before reaching out to your ex.

Remember that blocked numbers, read receipts turned off, or requests for no contact should always be respected. Persistence becomes harassment, and that helps no one heal or move forward.

The best messages come from a place of genuine care rather than neediness or manipulation. Focus on what you can offer (closure, friendship, co-parenting cooperation) rather than what you hope to get back.

Conclusion

Texting an ex boyfriend doesn't have to be awkward or regrettable when you approach it with clear intentions and respect for boundaries. The right message at the right time can provide closure, maintain necessary communication, or even rebuild a healthy friendship.

Remember that successful post-breakup communication focuses on personal growth rather than relationship outcomes. Choose messages that align with your genuine intentions and emotional readiness, not what you think might get the response you want.

Most importantly, respect all communication boundaries, including blocking, no-contact requests, and harassment laws. Healthy communication benefits everyone involved and demonstrates the maturity that makes any future interaction possible.

How long should I wait before texting my ex boyfriend?

Wait at least 30 days for emotions to settle, though 3-6 months is ideal for friendly communication without romantic undertones or heavy emotional baggage.

What if my ex boyfriend doesn't respond to my text?

No response is a response. Respect their silence and don't send follow-up messages. They may need more time or prefer no contact.

Should I text my ex during holidays or special occasions?

Only if you ended on good terms and enough time has passed. Keep birthday or holiday messages brief, genuine, and free from hidden agendas.

Is it okay to text my ex about getting back together?

Yes, but only if you've genuinely changed or circumstances have shifted. Focus on specific growth rather than just missing the relationship.

How do I know if I should text my ex or not?

Ask yourself: Am I emotionally ready for any response? Are my intentions genuine? Will this help or hurt both of us? If unsure, wait longer.