Dear Meagan,

I’m writing to try to repair our relationship by communicating as clearly as I can some issues I believe are hurting us in an attempt to work through them together. I love you dearly and want to make this relationship work, but if it turns out that our values and outlook are incompatible I think we’d both be better off knowing that sooner than later. I truly hope that’s not the case, but all of these issues have come up more than once so I believe it is best to call them out and try to address them head on.


Friends

I’m very proud of all the great friends I’ve made over the years. While I’m clearly an outgoing person, I don’t think the number of close friends I have is just a product of charisma, but also has to do with the fact that I genuinely look for what is good in people regardless of their background and put in the effort to maintain those relationships by making phone calls and plans to see them. These friends have enriched my life in so many ways including all the great memories we’ve shared together, but also in the network effects of introducing me to new hobbies, events, other new friends, and even new career opportunities. My best life includes many close friends and I plan on remaining open to forming new close relationships as I age. To that end, my best life will also include a partner who supports that side of me.

I know you consider yourself an introvert and also are unhappy in feeling you don’t have a great social network in Boston. I can appreciate that must feel lonely especially as I know you’d want more support going through this tough time at your job. I’ve tried to respond by including you in plans with my friends to try to allow you to tap into my social network. At both Kate and Tom’s wedding and our recent dinner party with Jack and Elektra I encountered resentment for having done so.  You don’t have to like all my friends and you don’t have to always have a good time hanging out with them, but I can’t be with someone who is resentful of the fact that I have many friends and want to share that with them.

The good news is everyone really likes you and immediately recognizes your kindness, so I’d invite you to step outside your comfort zone a bit in being more open to forming new relationships with people. In both the cases above, I believe you ended up having a good time in the end, so the initial resistance didn’t match up with the experience you ended up having. So you might find that opening yourself up a bit more in this regard could have unexpected beneficial results.


Class/money

I consider myself lucky to have come from a background where my parents were able to provide for me an upbringing where I never suffered from want and had many opportunities to see what the world had to offer. At the same time, they always impressed on me that having money doesn’t make you any better than anyone else and that it is your duty when you are fortunate to give back. Having more money than the next person is not a motivation whatsoever for me, but I also want to be able to provide for myself and my family in the same way they did. As far as my career goes, I do want to be an influential leader and help companies solve thorny problems and a fortunate byproduct of that would be that I’m compensated well for that effort. You and I both know how wretched it can be in this country to not have enough and I don’t apologize for never wanting that for myself or the people I love.

I sense that you have a moral judgement against those with money. I enjoy our political debates immensely, but it’s become more clear to me that you believe that money is primarily obtained through exploitation of others or the environment. That certainly does occur and is a major problem and I admire your fervor in wanting to address the ills in society that result from that, but I don’t agree that’s the main source from which wealth is derived and don’t believe others should be judged positively or negatively for what they have or haven’t got.

This doesn’t mean I want to go yachting with you (ugh). In general, I share in your desire to live simply and do judge others for gaudy displays of wealth. However, there are some experiences I want to have that do cost money, namely attending concerts/shows and travel, and I feel we’ve been doing some of those things less because of unresolved issues about how as a couple we approach handling money.

I also feel you might judge me and some of my friends for being of a different class than you perceive yourself to be or perhaps feel you can’t relate. I’m open to having people in our life from all sorts of backgrounds and would welcome more friends from less privileged backgrounds; I feel like noting I only have one friend I’ve kept from Weston and we bonded in part because we both didn’t really relate to the other spoiled rich kids we were surrounded with. That said, I can’t help that most of the circles I’ve traveled in have included upwardly-mobile people, which isn’t the same thing as being from a privileged background as some of my friends didn’t come from that much.

So I ask that you try to take a more nuanced view to class/money and try to judge people by their character and not where they came from.


Boston

Boston is a special place for me. At this point most of my friends are there and I’ve built a life for myself there that I truly enjoy. I love the waterfront and find many of its neighborhoods quite charming. In the long run, I will not want to live downtown in a city as I’d want a bit more space, but during this period of my life where I don’t have a family I’ve enjoyed feeling connected to a lot of things going on around the city and because I ride a bike, use the T, and am willing to pay for the occasional rideshare find the city to be incredibly accessible. In the long run, I’m flexible about where we might end up and I’ve generally expressed willingness to explore other places to live with you. That said, if I end up becoming CTO at Sports Innovation Lab, that will likely lock me into staying in the Boston area for 2-3 years.

You’ve expressed that you dislike Boston for a number of reasons. We’ve discussed your feeling like you don’t have a strong social network there, but some other major issues for you appear to be that prefer the feel of the country to the feel of a big city and don’t like transportation options there. I’ve proposed living in Cambridge as an improvement on those areas as Cambridge has a more relaxed feel, a car could provide access to the country on the weekends, and driving in general would be far less hectic. I do feel the need to note that most jobs in your chosen field (and in general) are in major American cities, many of which are more populous and whose transportation options are far worse than Boston, so I don’t know what alternatives you have in mind at this stage in your career.

Again, I am flexible in the long run as to where we might live and in the short run would be willing to explore other areas or ways to make somewhere in the Boston area feel more like home for you.


Response to stress

I wish with all my heart your job were going better and I wish you felt at home with loving friends who understand you. I’ve tried to be as supportive as I can and ask you how I can help or make things work better for you.

I’ve noticed that in response to stress, you tend to freeze up. I can understand wanting to avoid conflict and I can understand possibly being fearful in not knowing what to do, but the result is that issues can be left simmering under the surface which doesn’t make the situation any better. In turn, some of these issues have come to light at the worst possible time when we’re in a particularly poor state of mind to be able to do anything about it.

I ask that you try to be proactive in identifying issues that you’re feeling and where you can try to help identify possible solutions. I hope you can trust me to confide in me how you’re feeling and know I’m going to love and accept you and try my hardest to make things work. I also encourage you to talk with loved ones about how you’re feeling as it can always be helpful to have an outside perspective from someone who knows and loves you.

I also ask that you make an effort to focus on the parts of your life that you can control and can improve. I am so happy you’ve returned to Irish dance and would be excited to go to yoga classes with you again. I believe that as you exert more control over your life in those areas it will spill over positively to other parts of your life in a beautiful way.


Why I love you

I’ve said it many times because it’s true, you’re the kindest person I’ve ever met and your compassion is starkly obvious to everyone who comes into contact with you. You’re smart, ethical, hard-working, silly, and a total bombshell to boot. I hope you trust that I’m writing this to try to make things work between us and hope you want to do the same.


Sincerely,
Will