Q & A Wednesday: When Should You Give A Guy Another Chance?

Posted by in dating after divorce, love after 40, self-esteem in dating, single women over 40 | 0 comments

Dear Sandy,

I’ve been dating Jim for a few weeks. He’s a great looking guy, more handsome than most men I date. As a woman in her fifties, I have lowered my expectations for physical appearance in a man, but this guy is absolutely gorgeous. Blue eyes, a full head of hair, a runner’s body, and tall! I felt like I hit the dating jackpot.

But as we head to our fourth date, I am wondering whether I should give him one more chance. Let me explain…

After our first date, he began texting me. All day. During my work hours. Okay, maybe he was excited to get to know me, right? But then how do you explain his impatience when I didn’t immediately respond? He got pretty annoyed with me about that. That was my first red flag. Is this guy controlling? I wasn’t yet sure.

On our second date, he got angry at me about telling him to slow down our physical relationship. He raised his voice and was nasty and condescending. I was so taken aback, I was speechless.

The next day, I told him in an email that I didn’t like that he was a hothead and that he was not respectful of my sexual boundaries. He got defensive and didn’t apologize for the way he spoke to me.

He also changed plans on me at the last minute several times ~ without much of an apology.

It seems like every conversation becomes an argument.

I know I should probably not go out with him again, but he is so good looking and he’s a great kisser! We’re physically very compatible.

He also has a good job, which means a lot to me too, since my last boyfriend was bankrupt.

One more thing ~ he’s not the brightest guy, and our phone conversations are pretty dull. But I still feel bad telling him that I don’t want to see him anymore. I always want to give people another chance to redeem themselves.

We have a date scheduled for this weekend. What should I do? Should I give him one more chance or should I break it off now?

Baffled Betty

Dear Betty,

Some people will read your question and think, “Of course she should dump him. He’s an a-hole!” For others, it’s not as obvious. I share your question because it is quite relevant to the women to whom the decision is not clear.

Betty, it seems like Jim’s good looks and great job have skewed your ability to see and think clearly.

In order to make it easy to decide ‘should I stay or should I go’, you must first know who your are and what you need in a relationship.

If you haven’t yet come up with a list of non-negotiable character traits and values that you must have in a relationship, I suggest you do that immediately. I have written a lot about this topic. This article should help you get your list together: How to make a non-negotiable list.

I can guarantee you that angry, hot-headed, and boring will not be on that list. Unintelligent will not be on that list either.

Once you have your list, you should go back and check it after every date. If the guy doesn’t have the five things you absolutely must have in a relationship, it’s time to say next.

Remember, they are the five things that are essential to a good relationship with you. They are not negotiable. So don’t overlook them and shove them under the rug.

I have one more thing to say about this Jim fella. He’s a jerk. His character stinks. He would be a terrible boyfriend.

Character is the number one thing you should be focused on in dating. Dump him for being a jerk. No second or third chances.

Even though it may sometimes seem like there are no good men out there, trust me that there are other guys out there who have stellar character traits. Their looks will grow on you. People’s beauty, I believe, comes from the inside out.

So Betty, do not give Jim another chance. Dump him today.

And get back out there with your non-negotiable list. Be more discerning. Don’t allow men to speak to you in a disrespectful manner. You deserve much better than Jim.





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