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Ask ShanTell’em: He’s Broke!

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Dear Shan Tell’em,

I’m a single 44-year-old woman, never married, and no children. My last relationship ended because I realized we didn’t have the same long-term goals. Recently, I met someone online and we had an instant connection. I decided to meet in a public place and, shockingly, it felt like we had known each other for years. So what’s the problem?

When I started talking to him, he had just relocated back to his hometown. He had a job lined up and things looked like they were headed in the right direction. He lost his job and didn’t have anywhere to stay. He has lived in two different states in the last two months, and is now heading home AGAIN!! His sister said he could stay with her and use her car to get back and forth to work. He made a comment that I was not supportive of him and don’t understand what he’s going through. I felt hurt because I have paid for him to come home twice, been very patient, encouraged him, and tried to be understanding.

I know how I felt when I was down on my luck and didn’t have a significant other to confide in, and I am still here because I know he is a good man and really needs some positivity in his life. Financially, I have decided that he will have to figure it out from this point on. He has suggested that we end things until he gets on his feet. Should I let him go? By the way, he has asked that I not introduce him to my family because of his situation, and I have to admit I don’t want to introduce him to my family because of his struggles.


Dating a Broke Dude

Dear Dating,

We all have our tough times, and great partners will be there with you to weather the storm. But it sounds like another issue is to blame for the turbulence you’re experiencing in your relationship. The problem is not that he doesn’t have money or support, it’s that he does not seem to have a clear plan for his life. The constant traveling… why is it happening? Nothing seems to be settled about this man, so it’s no surprise that your relationship is experiencing the amount of havoc that it is.

I understand his reasoning for not wanting to meet your family. Any real man would feel a certain level of embarrassment if they do not feel like they can bring something to the table. It is very difficult to maintain a positive, healthy, loving relationship if you feel less than. It sounds to me like he knows that you are supporting him, and that is the problem. He does not want to need support.

Does he elaborate on what type of support he needs? It seems like you’re doing a whole lot, especially to be at this stage in your life. I do not know many grown women who would put up with such confusion. You didn’t mention how old your significant other was, but it sounds like he is making moves that someone in his twenties would make.

My advice would be to take space and let him figure things out. As difficult as it may be, it’s best to be with someone who feels like they measure up. Now, if and when he decides to opt for more stable lifestyle choices, and you’re available and interested, then have at it. But time waits for no one, and neither should you.

Good luck and I wish you the best.

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Shantell E. Jamison is a digital editor for and  She’s also a radio personality, and cultural critic. Her debut book, “Drive Yourself in the Right Direction: Simple Quotes on How to Achieve Your Best Self” is available now at