Imprisoned by Low Standards: When Your Love Interest Goes to Prison

Dear Gorgeous:

The person I love is in prison, doing ten years. He tells me it's okay if I fall in love with someone else, but for some odd reason, I meet guys who I feel are not on his level, are not worthy of my presence, or I find myself asking why did I even bother with this guy!

So, for the past three or four years, I've been in love with someone who's in prison, which means I've been by myself. I feel as if I have forgotten how to really connect with a guy on a level other than business! I need answers. Help me please!

-Stuck in Love

Dear Stuck In Love:

The first thing that struck me about your letter is your low level of expectation. You begin by saying you're in love with a man who is serving a ten year prison sentence, but follow up that statement by claiming the men you meet are not on his level––while he's in prison.


The truth of the matter is that the men you're meeting, the free, able-bodied men you're meeting are already a step above your love interest because they're not, well, in prison. But you're so hellbent on being with someone who obviously, at the very least, makes poor life choices. The question then becomes, why are you so attracted to someone who can't do something as simple as stay out of prison?

Good People, Bad Choices:

Good people make bad choices all the time, but so do bad people and frankly, I'm not interested in sticking around to find out which is which. Though I can't speak to this man's character, what I can tell you is that facts are facts and that man is in prison! He made, at least, one very bad choice and that choice didn't land him is jail for the weekend––it landed him in prison for ten years. Do you really want to be with someone who is prone to making this bad of a decision? Do you really want to build your life with someone who can, at anytime, have such a serious lapse in judgement that he puts himself and his family in danger, strife, and turmoil? Is this what you really want?

Possibly, this may be exactly what you want and if that's the case, good luck to you and I can end this commentary, here. But the fact that you're even asking for help tells me you know this isn't for you, that what you're doing is ridiculous, and that you're looking for an affirmation that will help you commit to making the right decision. What all of this tells me is that you are probably a good person who feels she is making a bad decision. Well, here is your mantra: If you don't know, the answer is no.

Raise Your Standards:

Low standards are a sign of low esteem and before you can raise the former, you must raise the latter. Though you have come to me looking for answers, you will probably find more questions here. Questions like: 

  • What is about you that makes you feel you don't deserve a better, more equipped mate?
  • Who taught you to hold on to things or people after they're already gone?
  • When did you stop believing there is more in the world for you?
  • How have you always imagined your life and why isn't that vision better than your current projections?
  • Have you ever learned the difference between love and obsession?
  • Do you live in your head because you feel incapable of living in the truth?
  • Are you making mostly fear based decisions?
  • Are you not making any decisions at all because of that fear?
  • Is it that other men aren't good enough for you or that you feel you are not good enough for them?

Let's take a closer look at that last question. It is already establish that, upon meeting any man, he is already in a better position in life than your current love interest because the man you have just met is not a ward of the federal government. He has, at the very least, avoided the kind of horrible decisions that can land one in prison for ten years! But, maybe he doesn't have the kind of personality you like, or the type of body. Maybe he's not as prosperous as you would hope or maybe bites his fork when he eats. Whatever it is that makes him not the right person for you, you are well within in your right to keep the relationship from going any further and continue your search for the type of man you want. But what do you really want? And are you  just nitpicking because you have so much work left to do on yourself that you feel the only person you're good enough for is the type of man who finds himself imprisoned for ten years?

Here's Your Homework:

  • Who Is He? Make a list of all the qualities your perfect mate will possess. Include trivial traits like the color of his eyes, the tone of his skin, and his build. Include the important things like his occupation, educational background, and political interests. Include his temperament, his hobbies. Make a list of all the ingredients you would use to build the perfect man for you. When you are finished, read over your list. I bet imprisoned for ten years isn't on it. Think about that.
  • Who Are You? Now, do the same thing for yourself. Make a list of who you want to be and include the same types of subject matter you added to the list about your perfect man. How do you want to look, where do you want to work, would you like to go back to school, where would you like to live, would you like to be more spiritual? Who are you when you are being your most perfect self? I bet keeping my life on hold for a decade for a man who is in prison won't be on that list.

Here's What Will Happen:

These are not just lists; these are declarations! Take a long hard look at what you have written and recite it, over and over until it all sinks in. This is what you want and, whether you know it or not, this is what you deserve. You don't have to live in a perfect world to have your version of a perfect life; all you have to do is focus on what you truly desire and stop at nothing until you obtain it.

When you begin asking yourself the hard questions and delving deeper into why you would ever consider putting your life on hold for a man who has proven himself to be a bad decision maker, ergo a man who is in no position to lead, you can start dismantling your fantasies and fears. After writing down your core desires, you will find that what you have actually done is pinpointed your desired destination. Now, all that's left to do is decide how to get there. I can't tell you how to do that, but what I can tell you is that you don't get to happiness by having low expectations and esteem, or by making poor life choices and operating from fear and fantasy.

In Conclusion:

The questions we ask are never about others, but are always about ourselves. This dilemma is not about your relationship with a man who is in prison, but about your relationship with yourself. When you get on the right emotional track, when you are so secure in yourself that nothing but the best will do, many of your questions will subside and things will become crystal clear.

Community Questions:

What would you do if you found yourself in the same situation as Stuck in Love? Would you wait for a man to whom you are not married? A man with whom you have no children? A man who put himself in the position to be in prison in the first place? Would you even be attracted to this sort of man or would a prison sentence be an instant turn off? Sound off below.

New York Times best selling author, keynote speaker and workshop leader, founder of The Gorgeous Girl's Guide, Steffans Publishing Enterprises, and Karrine & Co.