Why I Had to Stop Seeing Mr. Big After Our 5-Day Date

I wrestled with this experience for weeks.

I had to sit with it, talk with Mr. Big and ask questions, sit with it again, meditate, journal and talk to my confidante—all to process what turned out to be a very eye-opening and enlightening experience in more ways than one.

In “regular” dating, you usually go out with a person for one night and then return to your separate homes where you can reflect on the date and on the things discussed and observed, and make a decision about whether or not you wish to continue seeing the person.

When you go on dates that last 48 hours or more, you don’t have the luxury of space and distance to process the things that happen. You aren’t afforded the opportunity to truly think things through before you act on the information you are given.

You are stuck in the middle of the moment until the date ends, so you are essentially winging it and not always making the clearest decisions.

G/O Media may get a commission

Carncome Armchair

Buy for $204 from Wayfair

In hindsight, we both agreed that if we’d had it to do over, we would have made date No. 2 a lot shorter, but we were soaring on the high of date No. 1 in Vegas—and hoping to recapture that magic while spending as much time together as possible. However, we definitely overshot our plans for our second, five-day “date.”

As magical as Vegas was, there were a lot of things I now realize I should have paid closer attention to. Things that seem small in a whirlwind 48-hour period become magnified when observed over a five-day period, and those things become exacerbated when, as mentioned before, there is no processing space or time to sort them out.

Mr. Big is a generous person with a big heart who suffered a tremendous loss not long ago. He is still very much in the middle of grieving that loss and processing the pain that goes along with it, and that plays a tremendous role in his moods, actions and the decisions he makes.

I am empathetic by nature, and as such, I tend to also want to be a fixer. I want to make sure everyone is all right, and I want to help them solve their problems. This, however, was a problem I knew I could not solve. This was a person I knew I could not fix, and I realized right away that it wasn’t my job to, either.

I am still not sure where Mr. Big saw me fitting into a life that was as complicated as his is right now, and to be honest, I don’t think he is or was entirely sure, either. In our conversations after date No. 2, I asked him a few times what it was he wanted from me, and he was never able to verbalize it.

Suffice it to say that his grief and pain and the manifestations of both served as the biggest impediments to our being able to have anything truly lasting or meaningful. The heaviness of what he is going through is an encumbrance that I am not willing to take on as my responsibility. That is what therapists and mental health experts are for.

The grief and the pain are things that are out of his control. I don’t fault him for either.

But sometimes, when we are in pain, we inflict pain on others. Usually it is unintentional, but when it is pointed out to us, it is our job to make sure that we don’t continue doing it—no matter what we are going through.

Grief and pain can excuse bad behavior for only so long—after a certain point, it becomes willful.

In the end, although we were very attracted to each other, this just wasn’t our time.

As Kenny Rogers said, you have to know when to hold ’em, know when to fold ’em; know when to walk away, know when to run.

As much as we might want something to happen, we owe it to ourselves and the other person involved to understand when to let go.