Send A Retiree Off Smiling: 120 Retirement Wishes For A Friend

Struggling to find the perfect words to send your friend off into retirement? Look no further! This collection of funny, short, and heartfelt messages and well wishes is sure to inspire you. Whether you’re writing a retirement card or giving a toast at a party, you’ll find the ideal way to express your congratulations and excitement for their next chapter.

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Short Retirement Wishes For A Friend

Looking for the perfect way to send your friend off into retirement without a long speech? These quick and heartfelt wishes are the perfect solution! Ditch the cheese and express your congratulations in a way that’s both meaningful and memorable.

  1. I wish you all the best for this next chapter in your life.
  2. You’re the one and only legend! And you’ve retired! Congrats!
  3. You can’t retire from being great!
  4. Happy retirement! You deserve it!
  5. And so the retirement adventure begins… Enjoy!
  6. You only retire once, so make it count! And don’t do it twice!
  7. Best wishes for a magical retirement!
  8. May your retirement be filled with fun adventures!
  9. Enjoy happy hour every day!
  10. Welcome to your new life: eat, drink, nap, and repeat.
  11. Congrats on having a lifetime of weekends!
  12. Congratulations on your retirement. Enjoy the ride!
  13. It’s time to say goodbye to tension, and welcome the joy of pension!
  14. Time to make your dreams come true!
  15. May you have the time of your life!
  16. Life begins at retirement! Congrats!
  17. I wish you lots of health and happiness in the future.
  18. May your wildest dreams come true!
  19. It’s time to make that bucket list…
  20. I’m proud of you. You deserve to enjoy your retired life to the fullest.
  21. May you enjoy all the best that life has to offer.
  22. Best wishes on your well-deserved retirement.
  23. Wishing you a fun-filled retirement!
  24. May God bless you with a fantastic retirement.
  25. Enjoy your freedom.
  26. Best wishes for your retirement.
  27. You deserve all the best things in your retired life.
  28. Wishing you all the best in your future endeavors.
  29. Enjoy this new journey in your life.
  30. Congrats. Enjoy the longest holiday of your life!

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Funny Retirement Wishes For A Friend

Saying goodbye to a colleague can be bittersweet, but why not add a dash of humor to the mix? These hilarious retirement wishes are guaranteed to make your friend (and maybe even their soon-to-be-ex-colleagues) laugh out loud. Celebrate their escape from the daily grind with a lighthearted message that perfectly captures their personality.

  1. Retirement is awesome—you can finally do nothing without being worried about getting caught
  2. When “I want to quit” becomes your daily mantra, you know it’s time for you to exit and retire.
  3. Good luck with your new boss: your spouse!
  4. Free at last, dear friend.
  5. Retirement is like a long vacation in Las Vegas. What happens in retirement, stays in retirement! Good luck!
  6. The legend has retired, now what are you going to do? (Recommendation: Matching Gift)
  7. Retirement is not the end of the road; it’s the beginning of the open highway! Hit the road and enjoy the trip. Congrats, my friend.
  8. Yippee-ki-yay!! You don’t have to come to work ever again!
  9. Congrats, you’re officially retired from this crap.
  10. What do you call a person who is happy on Monday? Retired and unemployed! Pick one that suits you!
  11. You’re retired! Now you can do anything you want, as long as you receive permission from your spouse.
  12. Be happy that we’re not your problem anymore! We’re also happy that you’re not our problem anymore either! (Recommendation: Matching Can Coolers)
  13. Congratulations on making your employment transfer official. Good luck working under your spouse from now on!
  14. Hi-ho, hi-ho, it’s off the work no mo’!
  15. Thank God it’s Friday will become an everyday occurrence to you now!
  16. Retirement. The money’s bad, but the hours are excellent!
  17. You’ve made your mark and paid your dues. Now, put on your dancing shoes!
  18. You can beer all you want because you’re retired! (Recommendation: Matching Beer Mug)
  19. Congrats! You survived this hellhole. Go order a medal of honor from Amazon. We don’t have that here.
  20. Quitter! Oops, I mean, happy retirement!
  21. Now, your only job is to have fun, and I know you’ll be great!
  22. Congratulations on the world’s largest coffee and potty break!
  23. Retirement is the time when you stop lying about your age and start lying around the house, or the beach, or the park, or anywhere you’ll go!
  24. You worked your whole life for this, and that’s just sad! (Recommendation: Matching Mug)
  25. Watch out. Someone’s about to have too much free time on his/her hands…
  26. Retirement: The time you realize that being showered and dressed in the morning is not mandatory.
  27. Life in retirement is going to be an adventure; trekking through the garden, climbing out of bed, and diving into a good book. Congrats, and enjoy!
  28. Congratulations on sacrificing your health to earn more money to retire happily. Now you can spend all that money to keep yourself healthy.
  29. Congrats. Get ready to be showered with many chores from your kids, grandkids, and friends.
  30. A sage once said nothing. Are you expecting something? Get out of here! (Recommendation: Matching Quoted Gift)

Witty Retirement Wishes For A Friend

Retiring after years of service deserves a hilariously memorable send-off, especially for your close friend! Forget the generic well-wishes and unleash your inner wit with these clever retirement messages. Get ready for some serious laughter (and maybe a few groans) as you celebrate their well-deserved freedom from work.

  1. Retirement is just a nice way of saying that you’re getting too old for this!
  2. For someone as lazy as you, retirement will be the same. Just only now, you don’t get paid for it.
  3. You can’t teach an old dog new tricks but can put new tires on an old car. That’s what you’re doing: re-tiring. Enjoy your new wheels.
  4. Retirement is waking up in the morning with nothing to do. And by bedtime, only half of it is done. Congratulations on doing nothing just as you were before!
  5. Now you have time to whine and wine all day! Two things you’re great at! (Recommendation: Matching Wine Glass)
  6. Behind every retired person is a spouse wishing they would go back to work. Happy retirement!
  7. Congrats on your retirement. Now every day is Saturday!
  8. Enjoy your neverending weekend!
  9. You’re currently unsupervised. I know it scares me too…
  10. Do monarchies retire? I think not. Thankfully, you’re not a monarch! (Recommendation: Matching Insulated Tumbler)
  11. Congratulations on gaining two new best friends upon your retirement. YouTube and TikTok. Don’t let your brain rot!
  12. Now, you will never know if people are genuinely happy about your retirement or if they are happy that they finally got rid of you…
  13. Congratulations on finally deciding that life is more important than work! What took you so long?
  14. My retirement advice to you: just pretend you’re our boss. Doing nothing is their specialty!
  15. Retired. Under new management. See spouse for details (Recommendation: Matching Retirement Gifts)
  16. If you struggle to find something to do in retirement… Feel free to mow my lawn anytime.
  17. When people ask what you’ve been doing in retirement, try to lie about it… Because we all know that you’ll be lying around somewhere taking naps and sleeping.
  18. Happy retirement. Now Fridays aren’t the best day of the week anymore. They all are!
  19. The biggest challenge in retirement is spending time without money. Good luck!
  20. You’re not getting retired. You’re being demoted to a babysitter! (Recommendation: Matching Witty Mug)
  21. Congrats on your new job: living life to the fullest! You’ll be great at it!
  22. Soon, you’ll wonder, how did you ever have time to work?
  23. Congrats. There is no better feeling than going to bed and not having to set the alarm.
  24. Retirement is like a neverending vacation. Only you’re not fit for the most fun stuff.
  25. Goodbye to you, friend! I know you won’t miss it here! (Recommendation: Matching Funny Clock)
  26. Happy retirement! Now you never have to use the excuse of being sick when you’re playing hooky at the office.
  27. Enjoy sleeping in, knowing that we all have to go to work!
  28. Retirement doesn’t make you an old fart. It means mean you no longer give a shit.
  29. Congrats on your new skills in retirement. You can laugh, cough, sneeze, and pee all at the same time.
  30. Time to wine down and relax. Nothing’s changed, right? (Recommendation: Matching Wine Rack)

Heartwarming Retirement Wishes For A Friend

Retirement is a momentous occasion, and heartfelt words can make it even more special. These warm wishes celebrate your friend’s achievements and express your excitement for their next chapter. Whether you prefer a sentimental message or a balance of humor and love, you’ll find the perfect words to express your care with these retirement wishes ideas below:

  1. Retirement forecast: Doing nothing with a chance of napping. Enjoy it to the fullest!
  2. You’re not retired. You’re a professional grandparent! Have a great time with the kids!
  3. Stay young at heart, kind in spirit, and enjoy your retired life!
  4. The day has come. You finally stop working and start living! I wish you all the best in your retirement and enjoy all the adventures you have ahead of you. Happy retirement!
  5. The possibilities are endless. Have fun and enjoy every moment. You deserve all the best!
  6. Happy retirement! May your future include more of the things you enjoy and none of the things you don’t!
  7. All your hard work has finally paid off! Enjoy having the time to do all the things you’ve always wanted to do. Have a wonderful retirement.
  8. Life after retirement is like the second inning of life. Reward yourself with a great and joyous vacation that you’ve always wanted. Congrats, and enjoy your retirement!
  9. May you have a healthy and happy life with all your friends and family!
  10. Your beer is going to taste a lot better when you don’t have to work the next day. (Recommendation: Matching Retirement Beer Mug)
  11. As a chapter closes in your life and a new one starts for you, may your years be filled with all the things you’re looking forward to. Congratulations on your retirement!
  12. Wishing you a new journey of success and happiness in this phase of your life. May you be showered with abundant opportunities and do the things that your heart desires.
  13. The day you finally stop working and start living! Happy Retirement!
  14. Don’t act your age in retirement. Act like the inner young person you’ve always been! Congrats on your well-deserved retirement.
  15. Wishing you much joy and happiness as you begin a new chapter in your life!
  16. Dear friend, you know all those things we’ve talked about that you’ve always wanted to do? Now is the time to do them! Congratulations, and enjoy your retirement!
  17. You deserve the best retirement for your dedication and hard work. Enjoy this journey of your life. Cherish every moment and have fun!
  18. As you reach this time in your life, may you find joy in remembering past success and happiness in pursuing new hopes and plans.
  19. Best wishes for an awesome retirement. Keep working hard, but be your own boss!
  20. Now you’re finally in charge of your time and life! (Recommendation: Matching Wine Tumbler)
  21. May your retirement be filled with many new adventures, meaningful moments, and much happiness. Happy retirement!
  22. As you go into the next phase of your life, may you enjoy the best that life offers!
  23. Retirement marks the end of working for someone else and the beginning of living for yourself. Congratulations, and I wish you a happy retirement!
  24. After climbing the mountain, you can finally enjoy the view. Congratulations on your retirement! Enjoy the amazing view!
  25. Retirement is a time to look back with satisfaction and be excited about what is to come. And fill each day with enjoyment and activities you’re passionate about. Congratulations on this special time in your life!
  26. Congratulations on your retirement! Start listening to your heart; it’s the best gift you can give yourself when you retire.
  27. Look back and be proud of what you’ve accomplished. And look ahead with anticipation and excitement. Let your heart lead the way to many joyful moments in your retirement.
  28. Have no regrets about things you wouldn’t have done differently in the past. Retire with great ambitions and dreams for the future. Have a happy retirement!
  29. Congrats on your newfound freedom. The road to an even greater sense of freedom is personal growth. Have fun discovering new things about yourself. It will be a fun and surprising adventure.
  30. You can charge a consulting fee next time we talk. (Recommendation: Matching T-shirt)


No more scrambling for the perfect words! This treasure trove of funny, short, and heartfelt messages is guaranteed to spark inspiration. So grab a card, raise a glass, and craft the ideal send-off for your friend’s exciting new chapter.

Want to explore more ways to celebrate? Check out my other articles for fresh ideas on gifts, party themes, retirement speeches, and other retiree-related content. Here are some of the recent ones that I published:

Happy reading!


My wife and I quit the rat race and retired in 2021. We RV'ed around the US for a couple of years and now we're slow traveling outside the US!

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