I Have to Decide Between Two Women. Who Do I Pick?

Kara Pound

Written by: Kara Pound

Kara Pound

Kara Pound is an award-winning journalist based in St. Augustine, Florida. She holds a bachelor's degree in journalism from Flagler College. Her work has been published in INKED, Natural Awakenings, Design Aglow, Memphis Flyer, Jacksonville Magazine, E/Environmental Magazine, and dozens more. Check out some of Kara's work at karapound.com.

Edited by: Lillian Castro

Lillian Castro

Lillian Guevara-Castro brings more than 30 years of journalism experience to ensure DatingAdvice articles have been edited for overall clarity, accuracy, and reader engagement. She has worked at The Atlanta Journal and Constitution, The Gwinnett Daily News, and The Gainesville Sun covering lifestyle topics.

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Reader Question:

I have to decide between two women. Please know, I am not by any standards dating either one of these women, and neither of them know of the other yet. I ask for your decision because I have tried many times in the past and have either failed miserably or have been drastically let down.

With the first woman, I could see our whole lives together. We met three weeks or so ago. We have a great connection, and I know it could be something real if we want it to be.

The other woman I have known since I was 14. I would move the earth if it meant her happiness. We got close to becoming more one day but both choose not to. We both watched and helped each other go through one bad relationship after another.

She left a message on my page reminding me like in the old movie that if we are both 30 and not married, we should do it. Then she backed off. I know she got scared that she might fall in love and I would hurt her like so many of the other men before me who screwed up. I backed off also.

We are talking more and things are getting back to maybe being together again.

I know that if I want the first girl, she is all mine and I would be all hers. In the same token, I know I could love the other woman our whole lives, but I have to make her realize that I am going to be there for her no matter what the case.

So I ask, do I take the chance and go with the new girl that could possibly be the girl I have been waiting for my whole life, or do I try again with the girl who has been in most of my dreams since the day I knew her?

I know rushing into a relationship is bad, and I won’t be rushing with either of these two women.

-Jason V. (New York)

Expert’s Answer:

Hello Jason,

To make it easy on ourselves, let’s tag the women as New Girl and Old Girl. That will simplify things. Am I correct that you have only known New Girl for three weeks ? If so, then why would you even be considering spending the rest of your life with her? First off, you don’t know her. Second, that would probably scare the bejeebers out of her and could lead to a possible restraining order.

Now, let’s talk about Old Girl. You’ve known each other for a while and it sounds like you’ve cared enough to keep a relationship going through all these years. It also sounds like Old Girl could be your soul mate. What do you think?

I would ask her to sit down and talk, and approach her with the same honesty you approached this letter with. Tell her you’ve loved her since you were 14, you’re done dating around, and you’re ready to admit to the girl of your dreams what she means to you.

Good luck!


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