Does He Deserve a Second Chance?: Guest Post

second-chanceIt’s hard to find a woman who has not been scorned, or to be a bit more blunt, screwed over by a man. It’s just as hard to find a woman who has not at some point “overlooked” this and given the same man a second chance. Second chances leave many of us shaking our heads and rolling our eyes in horror at the thought.

The thing is, everyone is different and not all mistakes are the same, so how do you decide if he deserves a second chance?

Does He Deserve a Second Chance? How Many Chances Are Too Many?


In my humble opinion, there is a huge difference between being forgiven and being stupid. Sorry, but it’s true. For example, a man who continually feels the need to seek the “affections” of other women when he claims that you’re his one and only, should be kicked to the curb. He won’t change. Move on.

But, what if it’s a onetime thing? This may be a different story. I’m not condoning cheating, but people do make mistakes and often there are mitigating circumstances. Only you can decide if the circumstances warrant forgiveness and a second chance. But be honest, can you really forgive and move past the transgression? Because if not, the second chance won’t matter and you’ll only continue to prolong the pain.

Abuse (Physical and Emotional)

Easy. No second chances, ever.


I’m not a big fan of lying and don’t surround myself with people who make a habit of it. But, we are all guilty of omitting things from time to time and changing a story to serve our purpose better. Is it okay? No, but it happens. What did they lie about? Only you can assess why the lie was told and determine if it’s forgivable and worthy of a second chance.

Be honest with yourself.

Staying for the Right Reasons? Let’s Get Real!

Why are you considering offering up a second chance and staying in a relationship where things aren’t all you hoped? Only you can honestly answer the question, so be honest with yourself. Are you staying because you truly, deep down where nobody is looking, believe he’s the right man for you? If so, give it a chance. Can you picture a healthy, happy future based on what is, not what you want the relationship to be? If so, give it another chance. Are you staying because you are scared to be alone or because it’s comfortable and you don’t have time to invest in another relationship? Or because nobody will ever love you like that again? Those reasons are not good enough for second chances because they are not signs of a healthy perspective. Move on.

I need to throw in a caveat here. Second chances when dating and second chances when you have made a bigger commitment, like marriage or parenting are different. The ramifications of staying and leaving are far greater and complex and I won’t comment on what’s best in those situations. Although, if the infraction is one of the above, you have some thinking to do.

You Don’t Know What Ya Got ‘til It’s Gone

I have no idea why men ask for second chances after they have royally screwed up but I have two theories. First, they really did make a mistake; they know it and are remorseful. Second, they enjoy the drama and are keeping you around for some of the reasons listed above. How do you know? You just know.

Just Be Honest With Yourself!

Hilary Wynne is a contemporary romance author living in Northern Virginia. She is a business owner, wife (to a man she gave a second chance), and mom of five. Hilary loves talking and writing about all things relating to romance and dating, so head on over to her blog for more thoughts. 

Your Sister in Dating Bliss,

Single Dating Diva

Copyright Single Dating Diva


    • Thank you! Unfortunately some people like the drama. That’s a whole other post though, right 🙂 I think when we listen to our gut instincts we can tell the difference!


    • Thank you! I really feel that when we are honest with ourselves (which isn’t always easy), the answers will come. Not everything is black and white and some healthy introspection goes a long way.


  1. You touched on an important point…his nature. If it’s a mans nature to be a liar, cheater or abuser, move on. Reclamation projects don’t work. However, if he is a good man who made a mistake, I’d strongly recommend forgiving him. Many men will grow and develop through failure, and actually develop character and integrity through the process. The very important part that you play is this….If you honestly choose to forgive him, forgive him and never use the incident against him in the future. If you will commit to this, he will love you for it.


    • Thanks for the feedback! I speak from personal experience on this one. I gave my husband of 18 years a second chance after he failed to share some VERY important information early on. I believed he was a good man who made a mistake and I was right.


      • It really does depend on the situation and what he did. For you Hilary, it turned out for the best. It’s important to think critically and listen to your gut before making a decision.


        • Could not agree more. I might have failed to mention that this second chance was NOT given easily 🙂


    • Hmmm.. can’t agree with you here. I gave my husband a second chance and it was one of the best decisions I ever made. We weren’t married at the time and had only been together for two months. I chose to trust him and it has lead to a great (not perfect, but really really good) life and an amazing family. Some people thought I was nuts, but I trusted my instincts and they were spot on.


  2. Completely 100% agree. I have seen and concluded that no matter what support you may receiving, emotional, financial, etc., any time something happens that requires a break up (especially in dating) a second chance only reinforces that behavior.


  3. One of the saddest things to watch is someone who repeatedly puts up with bad behavior. They endure this usually because they don’t want to deal with the heartbreak. Or they get some psychological payoff that is outside of ‘normal’.

    And after a 2nd chance, a third chance, a fourth chance, well, you’ve given someone a license to treat you like crap at this point. They know they’ll get away with it and the person will take them back. And I see this behavior in people well into their 40s and 50s.

    Sometimes you have to make take a gut shot at forgiving someone. But repeated chances, well it’s just sad to watch.


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