Dearest Monkey,

I started seeing a new therapist last week because my other counselor (the one I started seeing a month or so before you left me) felt like she didn’t have enough time between raising a two year old son and taking care of her sick mother to be as available as she thought I needed.  This new psychologist is very kind and seems very knowledgeable, but I’ve only met her once so we’ll have to see how it goes.  Anyways, in our session she told me that in her experience with couples that is is often harder to transition to marriage from dating after longer periods of time like four or five years. She said that while it still happens, it is more common for people who were married within the first two or three years of their relationship to push through the harder times that come later in a relationship than it is for people who are married.  She gave me a number of reasons for this, but the biggest two were that people are more committed to working with their partner’s flaws if they are tied together by more than just their love, and that when people have been together for a long time without marrying each other, they built up marriage to be something different than just living together, and while it is legally different, it doesn’t actually look any different on a daily basis.

I’m telling you all of this because I’m afraid that I waited to long to ask you to marry me, and that in the process of waiting I lost you and I lost my chance to be with you.  I can’t help but wonder if I things would have gone down differently if I had proposed even 3-6 months earlier, like when you were looking up engagement rings on the internet and I laughed at you. I’m sorry about that. If I had asked you then, would you have said yes?  Or if I had asked you on our trip to Nicaragua or sometime around there?  I feel like I missed the window by possibly as short of a time as two to three months, and I keep kicking myself about it.  Would you have said yes if I had asked you a year or two earlier?  Or even if I had asked you in September when you said that you originally wanted to know if we could marry after officially living together for the first time ever?  I will forever wonder about that, and forever kick myself for not asking you sooner, because I strongly believe that you would have said yes had I asked you sooner than five years into the relationship. That is, and will remain, the biggest question mark of my life, as well as the biggest source of regret behind our final night together, which never would have happened if I had gotten my act together sooner.

I miss you still, and it stings as much now as it did on that fateful night. I love you too, and I always will. I hope you know that.

Always yours,


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