Secret Regrets of Women in Their 30s

Secret Regrets of Women in Their 30s

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Regrets, we’ve had a few. And apparently, so have many of you. A while back, Kevin Hansen, author of the bestselling book “Secret Regrets: What if you had a Second Chance?” shared with us the secret regrets of women and men in their 20s, submitted anonymously to his website, Secret Regrets.

Many of you clamored to know what those in their 30s were keeping a deep secret, so we went back to the man who knows. Hansen scoured his archive of over 10,000 regrets, and compiled a list just for us: the deep, dark, woulda-coulda-shoulda’s of women in their 30s.

Although we may be a little older, some of us are not that much wiser. Many of us still find ourselves “trapped” in relationships we know we shouldn’t be. We rue giving in to temptation. And we regret not being the kind of friend, daughter, wife or mother we had hoped.

Start reading below, and we think you’ll agree: Some of us are a bit of a hot mess; others are one step closer to figuring it all out. Either way, it’s all highly entertaining.

Top 20 Secret Regrets of 30-Something Women

1. I regret encouraging you to move to my neighborhood. Truth is, your husband is incredibly hot and if you did move here, I think I could get him to cheat on you with me. I don’t want to test that though. Please stay where you are. — Female, 30

2. If I had a second chance to do ONE thing differently in my life, I would never have slept with him, because then I wouldn’t have spent several years afterward checking my son’s features for similarities to him. I know now that he’s my husband’s son, but those were some awful years, not knowing. — Female, 36

3. I regret divorcing my husband, and then wanting to vent about it with my best friend. Because, the problem is, they’re both the same person. — Female, 33

4. I regret not leaving you when our first child was 3. I regret that I felt I had no other way out because we had a child together. The night of our major fight we had make up sex and I got pregnant again, and I stayed again. After 2 years of being separated you tell me you want to work things out. As much as I may want to get back together for the kids…I don’t want to regret staying again. I’m sorry but it’s too late. I’ve moved on. — Female, 39

5. I regret using shopping as a way of dealing with my unhappiness in the past. Now I’m truly happy in my life situation, but my past mistakes are still being paid for, literally. I regret that I will still be paying for my past unhappiness for many years to come and that I feel like I’m completely drowning in debt. — Female, 33

6. I regret that because of the pain you have caused me, because you can’t be anything but selfish, because you are continuing the affair and denying it, that because of all of those reasons, I’m going to wreck myself and have an affair just to hurt you. That because I feel like an outsider in our marriage, someone who is ugly and not worth love, I’m going to seek attention elsewhere. I don’t regret the hurt I’m going to cause to you, but I will regret that all my morals are disappearing in my desperate need to feel loved. By anyone. I regret that I’m not going to be the same honest, faithful person I was, because of you. — Female, 35

7. If I had a second chance I would not have had a retaliation affair. When I confronted you about stepping outside of our marriage you were horrified, and did everything possible to try and make amends, even marriage counseling. I couldn’t bring myself to forgive you. I wanted you to experience the same indescribable pain that you had caused me. So, I cheated while I was on a week long vacation with friends. I am so ashamed of myself, and don’t think I will ever be able to tell you. I should have just left things as they were. I feel worse now than before I strayed. This wasn’t a victory. I didn’t get the smug satisfaction I thought that I would by sleeping with another man. — Female, 32

8. I regret having loved you…and I thank God everyday for his unanswered prayers. I am so glad you are gone, and now someone else’s problem! — Female, 38

9. If I had a second chance I would have done it. I would have joined Americorps, or taught English in Japan, or driven across the country with a friend, it doesn’t really matter what “it” is. It’s more what I wouldn’t have done. I wouldn’t have chosen what I knew over what could be. I would have been brave instead of seeking comfort. I would have left a relationship that was leaving me anyway. Now I wonder what could have been. Where I could have gone, what I could have done, who I could have been, what I might have accomplished. Mostly I wonder if I’d have a better sense of myself if I’d given myself the chance to explore the world and compare, instead of staying in the place I knew to become stagnant. Now all I can do is move forward and urge others to do the same. Funny thing, I don’t regret anything I’ve done, even the mistakes. Just the things I didn’t. When presented with a “should I do it?” moment, please say, “yes.” Do it. Do it well. Don’t look back. — Female, 33

10. I regret getting so comfortable in my marriage (which ultimately failed) that I let myself go and now, as a single mom pushing 40 and 300lbs, nobody wants me and I’m facing a life utterly alone and lonely with no way to change it. — Female, 38

11. I don’t regret having given you permission to end your life … I still feel that I was right to give you strength in knowing that your friends and loved ones would forgive and understand that you couldn’t allow yourself to linger and make them suffer with you for the final stages of AIDS. I do regret not having been there for you more in the months between when we had the conversation and when you did it.

Most of all I regret that it’s been just over a year and I haven’t kept my promise to tell our friend how much you loved her and wished you could have been a man with a future, one who could give her the life that she deserves with a white picket fence and fat babies and all the rest.

Every day I try to write that e-mail, or figure out in my head how to say it to her, but my eyes go blurry with tears and I just can’t find the words. What if she felt the same way, and letting her know what she could’ve had, if things were different, hurts her as much as it hurt you knowing that it could never happen?

How do you tell a girl that her best friend loved her most of their lives, but didn’t realize it until he’d already done the things that made it impossible to offer her more than pain and suffering? It’s been just over a year and still I have no words. As much as I fear that knowing will hurt her, I fear even more for HIS sake that it won’t. He’ll never know how she felt and whether she would regret the missed chance, but I think if I found out she never cared it would break my heart. — Female, 31

12. I regret getting married to my high school sweetheart. We should have never decided at 17 that we should be together forever. I regret not living on my own for a while just to know I can do it. I regret letting you choose where we live because I hate it here. I regret living my days as numbered just waiting until the kids are gone so that I can be too. — Female, 39

SECRET REGRET: I regret living a lie for almost a year, even though I know I would be happier without you, I stick around for the kids’ sake and fear of the unknown. The other problem is that you know I am intimate with someone else and you seem to be okay with that idea, as long as I don’t leave – but I love him, not you. When our youngest graduates high school, I will be finishing my Master’s degree and leaving. I count the days until my life will be free of the overbearing, controlling relationship I’ve been forced to remain in for over 10 years. 709 days remaining, and I will be free from you and ready to start my new life. — Female, 35

13. I regret I became so close to you in my younger years. Now you think I have to tell you every tiny detail about my life, including who I am in love with, who I am dating, what I ate for dinner, where I spend my money and why I post certain things.

As I have grown older I want to keep secrets. I don’t want to introduce you to the man I am dating right away. I don’t want to tell you everything. I don’t even want to talk to you every day. I want to keep things more quiet in my life.

I am sorry Mom but I am a GROWN WOMEN now. Please do not push me away any further by treating me like I am still 18. You are no longer my only friend. — Female, 30

14. If I had a second chance to do ONE thing differently in my life, I would never let you convince me that our friendship would never transfer into a lasting romantic relationship, that we would never work. Because 10 years and two marriages later I still long to hear your voice in my ear, have your hands touch my skin, and be fully enveloped in your love. I never expected to want you, to need you, to miss you as I have all these years. You are my best friend but you should be my husband. You are my confidant but you should be my lover. You are a hundreds of amazing memories but you should be the father of my two children. I will love like no other and be with you when ever I have the chance. You will always be my destiny and is sucks we are both married to other people. — Female, 38

15. If I had a second chance to do ONE thing differently in my life, I would not have put my job before my family because it gave my husband a reason to have an affair and I totally understand it now. Not that it makes it right, I just understand that he wasn’t the only person to blame. — Female, 38

16. If I could do one thing differently, I would never have kissed him. I would never have allowed him to come over that night. Then he wouldn’t have awoken a part of me that I killed a long time ago. We want different things in life. It will never work. Yet I love him like I’ve never loved another. — Female, 38

17. As much as I love family and my life now, all these years later I still wish I had kissed him. — Female, 31

18. I regret that I cannot forgive and forget all of the pain and misery you caused me. I try to pretend that a mother is not capable of the destructive behavior you acted out and forced us to survive through. I will never be normal. I only partially look forward to having a child of my own someday, if simply just to allow them to live the life I never had. I have to hide all of my wedding plans from you. I am debating having any member of your side of the family there, in case you decide to show up and ruin my day. I wish I had moved to Dad’s at 4 instead of 13. My emotional stability would be much less compromised. It eats me alive to see mothers and daughters that share so many precious moments together, as much as it hurts to go through adult troubles without a mom to lean on. Shame on you. Shame on me. — Female, 38

19. I regret telling him I was pregnant. We barely knew each other and I was only 20. I thought I was doing the right thing. She’s 11 now and he has done nothing but harm her. The first time he kidnapped her, she was 2. The last time she was 6. It took me 2 years and $100,000 to get her back, all the while she was being physically and emotionally abused. Over that time he convinced her that I didn’t want her, that I wasn’t trying to contact her, that I drank when I was pregnant with her, and new lies are still being uncovered. This one regret has made me realize how insignificant any other bad choice in my life has been. I pray to God that I can mother her the way she needs, and that she will someday be a successful adult. Today I found her FB page… I think I’m not succeeding. — Female, 31

20. I regret that my mother is gone from this world & that my sister & I are left with a father who could care less about the fact that he’s slowly killing himself and that he is too selfish to realize what it’s putting me & my sister through. I regret that I have a father who is so selfish that he doesn’t care that although he is our only parent now, he only cares about the pain, suffering, and loneliness he feels and not that we may feel the same way, since we loved my mom dearly too, he just wants it all to end. I regret that I am slowly getting to the point where his selfishness is making it hard for me to care anymore when we get the calls from the ER. I regret that I am slowly getting to the point where I no longer care that my father is killing himself. I regret that because of this sometimes I wish he was the one who was gone & that my mother was the one still here. — Female, 32

21. I regret not being there for you when you needed a friend. I regret not contacting you for a few years before you took your own life. I regret not visiting your grave for over two years. We were best friends for years, sisters really – I can’t help but feel that I failed you.

I look at your suicide note and am filled with regret, even five years later. I regret that my daughter will never know you. I am ashamed that this isn’t the only time I failed you.

The entire world regrets losing your beautiful face, your sarcastic personality, your ability to always make everyone laugh. I love you and miss you Shorty. — Female, 33

22. I regret that’s my marriage has turned out like my parents. We stay married for our daughter and financial reasons but neither of us are brave enough to admit it. — Female,34

23. I regret that I don’t regret you. The way you have been after me, ever since the day I told you we could not do this, not while I was married – ever since that day I have wanted not to feel. I regret that I can’t get there. Even when you follow me around in your car, when I’m running or buying groceries or just living my life – even then, when every person I know says you are stalking me, I can’t regret you. I can’t get to you, and I can’t get loose from you, and still, I don’t regret you. I love you, and I miss you, and I wish things were different. I don’t know if that means I regret my decision that night, but I do know I will always regret where we have gone with it. If ever you would just stop that car, and talk to me instead of following me and staring at me, I would be so happy. We could resolve these issues, and no matter what it meant – a friendship restored, a real try at a relationship, or just peace for us both, I think we would both better off. Please? — Female, 38

24. I regret not being confident. I regret listening to the comments made by others. I regret my mother agreeing with those comments and not defending me when friends and family made them.

I regret that they made me feel like I wasn’t pretty enough or good enough in general.

Most of all, I regret that now, when I know I am beautiful and smart and funny and worth being loved – I still have that thought in my head that tells me I’m just not good enough. And that that thought stops me from ever letting anyone love me, letting anyone in at all. I regret that I think I will always have a little hate for myself deep inside. — Female, 30

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Secret Regrets of Women in Their 30s

time to read: 12 min