Asking Sunshine: Dating While Friends

Asking Sunshine

I have had an on-again, off-again kind of relationship with a guy for about three years. Recently, we have tried to really make it work for real this time, but the results are an interesting mix of chaos and harmony, with the chaos being explosive arguments, digs under the belt, and me trying hard to be better FOR him. My spirit is LOUD in telling me we’re not for each other, but there is so much history there, and I love him at the very least as a close friend. How can I get over this ideal of a relationship with this guy when I KNOW it will never work and without burning that bridge completely with someone who could still be a great friend? Or should i just let it all completely go?

Dear LOUD Spirit:

My first thoughts are run for the hills.  Anyone making you feel bad about yourself does not equal healthy in my eyes.  If you find the arguments get personal and/or you end up as the one looking “to be better for him”, your spirit may be loudly telling you this type of love can’t help build you up or help your self-esteem.

Really take a moment and think about the root of these explosive argument or digs under the belts.  How have they helped or hurt so far in your relationship and within yourself?   One thing is clear to me; something about this guy continues to draw you back.  Seems like there is this desire to “make it work”, even though you admit it never will.  That desire may have a lot to do with your romanticizing the outcome of the relationship each time you are apart from the relationship.

I’m not saying necessarily that this is what you’ve done, but let me tell you a story. In my early 20s, I was back and forth with a guy; I felt “if we could just stop fighting;” we would be perfect.  I began to romanticize about the “what if” every time we were apart.  But, when we were together, we found ourselves making arguing and chaos our norm.  The truth was when we were together it was nothing like the story I made up in my head while we were on break.  So, my advice to you is to listen to that LOUD spirit and see this for what it is (a relationship coming to its end).  I know this may be hard to hear but the end may be near, before you or he gets any further into the habit of hurting one another.  Chances are you’ll feel relieved once it is over and while there are sure to be hurt feelings (possibly heartbreak on both parts), if you’re kind about it, and straight up, maybe in time you guys can save the friendship side of things.

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In case you decide to stay:

If you are on again, consider sitting down and discussing the issues at the root of your break ups.  Determine if you are both on the same page with current relationship issues and future goals for the relationship. If past issues can be worked out in a healthy, appropriate manner, there is potential for your relationship.

If you’ve decided that you want to move on:

 Don’t leave the status of the relationship unclear or hint at a potential reunion.  Find closure by being honest.  If after this decision is made you find yourself in the conversation of “let’s get back together”, then you may need to stop contact altogether.

All that said sis; don’t forget you know what your spirit is telling you.  Listen!


Are you torn, unsure what to do next let Sunshine offer you some advice on addressing the maintenance and improvement of interpersonal skills, relationships (intimate, friendship and more). You can direct your questions to , please put “Asking Sunshine” in the subject line or if you are interested in being anonymous to me as well, you can submit your question to


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