Nine Years in, One Man Shares His Story of Marrying an Older Woman

Nine years ago I got married. I was 23, and my partner, Chimene, was 37.

Sometimes I get asked if I would recommend marriage for someone in their early 20s. I answer "no" every time. But then again, I would rarely recommend marriage anyways.

"On our wedding day. February 29th, 2008" Image supplied.
"On our wedding day. February 29, 2008." Image supplied

I remember a small snippet of conversation with my now father-in-law a few days before Chimene and I got married on Bernal Hill, a few blocks from our house in San Francisco.

He said, “Son, you are getting married, huh? I had no idea what the hell I wanted when I was 23.” Neither did I, but it just felt like the right thing to do at the time. So we went for it and had a small ceremony on February 29, 2008 with about ten people.

I had moved from Germany, where I grew up, to San Francisco in September 2006—only about one-and-a-half years earlier at the tender age of 21. Originally, I planned to stay in SF for one year and then go back to Germany to go to university but it became clear quickly that I wasn’t going to move back anytime soon. I wish I could say that love kept me here, but I didn’t even know what the four letter word meant back then.

I always had an issue emotionally attaching to people on a deeper level. Sure, I had good friends, girlfriends and of course my family, whom I all valued and felt loving and caring towards. And sure, I felt the butterflies and excitement of a new partner and lover, trying to figure out how to maximize compatibility and pleasure.

But I had never really felt that deep, earthy, rooted feeling of love that others were talking about. I discovered that years later.

To be clear, this is how it looked at the time.

Philip: 23-year-old German startup founder. Moved to SF with a couple of boxes of stuff. Very focused on work. Like every-waking-moment focused. Drinking the startup Kool-Aid. Techie. 6’ 3”. Introvert. Knew one person in SF when moving here. No alcohol, no drugs, no partying. Watching sports was thought of as a waste of time.

Weekend past-time: hack-a-thons and working on his startup.

Me at a trade show for my company in 2009. Image supplied.
Me at a trade show for my company in 2009. Image supplied.

Chimene: 37-year-old executive assistant. Had a career in hotel sales and decided to give it up to "semi-retire" into a job as an executive assistant. Now working only as much as needed in order to enjoy life. Owning her own house in the SF Mission District. Latina. Extrovert. 4’ 11”. Loves going to happy hour with friends. Season ticket holder of the 49ers and Giants.

Weekend past-time: watching sports and going out with friends.

Chimene at AT&T Park. Image supplied
Chimene at AT&T Park. Image supplied

When we married, we were officially dating for six months and had lived together for four of those months.

If you think this is a potential recipe for disaster, you are right.

There are broadly two struggles that we have encountered so far during the nine years that we have been married. The first is around our differences and how to appreciate the "otherness" of each other and not go batshit crazy in the process. The second is the age gap between us, trying to make the large age difference work. Sometimes these two struggles overlapped and seemed one and the same.

Chimene didn’t realize what it meant to be with a startup founder in Silicon Valley who was 100 percent focused on his company; and I didn’t know what it meant to be with a woman who left her traditional career path behind to enjoy life, hang out with friends, travel and watch sports.

She wanted to go to happy hour, Giants games and hang out with friends. I saw this as a waste of time and productivity. I wanted to buckle down and focus on building my business and talk about, well, my business.

I was hoping to have a partner who was as driven as I was, and she had already lived that part of her life before we met.

"I actually left the house for Halloween in 2008 but I am most certainly drinking cranberry juice." Image supplied.
"I actually left the house for Halloween in 2008 but I am most certainly drinking cranberry juice." Image supplied.

It was perfectly normal for me to skip dinner and work until two in the morning without letting Chimene know. I was working on important stuff! No time to interrupt! And I would get home at some point, so why worry? Chimene felt lonely and not important enough while also disagreeing with the idea that working 100hrs per week is a good mode of operating. I was pretty thick-headed and was not easily going to change my stance on this topic.

I actually resented Chimene and other people in our life for ending the workday so early and going out with friends.

Chimene is a huge sports fan. In fact, she’s had season tickets to the 49ers and Giants for years. We had to plan our vacations around the playoff schedule as well as the first home game a few times, and to say that I “didn’t get it” is an understatement.

"Same shoe. Different size." Image supplied
"Same shoe. Different size." Image supplied

We both compromised—at times over-compromised—during this early time of our marriage in order to have a compatible schedule. I reluctantly joined parties or friends/family events when I had to and she gave me a pass to work when it didn’t seem worth the fight to drag me somewhere.

Over the years, she came to accept times when I was really digging my heels into a work problem and as a result might skip a social obligation or our regular bedtime. I also know now that I can’t go full-steam indefinitely. I had a couple of burnouts over the years and it was not great for me, my work or my relationships.

As a result, I am much more levelheaded about when I might need to "disappear" for some time. With proper communication (a simple WhatsApp or phone call), this is not a problem for us anymore. Plus we know that it will not last for an indefinite amount of time. I still love building things and products and working with awesome people. But I also love spending time caring for myself physically and mentally, playing music, dancing and being with my friends.

As for going to watch the local teams: We have settled on going to one or two baseball games a year together. That way I can be excited to spend time with Chimene doing something she loves, and she can be excited about the fact that I truly want to join her. Often we leave before the game is over, but we both appreciate the time spent together.

"At a Giants game in 2015." Image supplied
"At a Giants game in 2015." Image supplied

Living most of my 20s married, I felt like I was not able to have the full breadth of experiences someone in their 20s gets. Whereas, she spent her 20s doing things that people in their 20s "normally do". She experienced things I could never experience. As a result, I felt like I was having to leave something behind to be with Chimene and live in the agreements of our marriage. I couldn’t just go and travel for half a year. I couldn’t date random people and collect many sexual experiences. I couldn’t just move in with a bunch of other hackers and makers somewhere and spend day and night building cool shit. In short, I couldn’t go wild and do crazy, far-out things because I wasn’t only responsible for myself but also for our relationship and her as my partner.

As stereotypical as it might seem, going together to Burning Man in 2011 was what triggered a lot of these insights and acted as a pressure cooker for how we related to each other. It brought out the challenges and differences that we carried around with us.

When I said things like, “Wouldn’t it be great to live with this group of people and build cool stuff?” or, “I want to have those experiences you had!” I was often met with a frown and a questioning of whether I actually liked living with her. She understood that I felt I was missing out, but the agreements of our marriage didn’t support that arrangement. Eventually we decided to go to therapy to figure our shit out.

"Burning Man 2011" Image supplied
"Burning Man 2011". Image supplied

It is said that love knows no age. But our bodies do. And the biological clock is real.

The topic of children and having a family came up very early on in our relationship. Even though we both didn’t want kids initially, the time seemed right for us a few years later and we decided to try to have a child.

I was 28 and Chimene was 42. We were able to become pregnant, but ended up losing the pregnancy mid-term. I have previously written about this gut-wrenching time and the year following it. This experience started to shift my mindset around life, work and love and drove the point home that my dreams, or life for that matter, can be over at any time — even if I "did everything right".

Chimene and I dealt with our grief in different ways and for different periods of time. I was ready to continue on with life much earlier and I tried to support her in dealing with the loss but rarely succeeded. This made our relationship very difficult because I was "ready to move on" and push forward with life while she wasn’t. We worked hard to not let the chasm between us become unmanageable and months later, we tried to conceive again with no luck.

Eventually we started talking about donor eggs and adoption, and I noticed that somewhere along the way the whole dream of having a family died completely for me. I wasn’t fully on board anymore. And being "half on board" for this kind of thing is never good.

When I finally said “I don’t want to have kids anymore for now”, all hell broke loose. And rightfully so.

This was the last chance for her to have a family with a baby of her own. I felt terrible because I had strayed so far from what was our shared dream together, but knew exactly where I stood. It didn’t make it easier that I was the one who originally suggested we try for a baby a few years prior. Where would that leave her, our marriage and our relationship, if I was to change my mind again and actually wanted kids later on?

"Climbing in New Zealand." Image supplied
"Climbing in New Zealand." Image supplied

This happened about a year ago and it still is a tender topic for us. Again working with a therapist, individually and as a couple, helped us digest the experience of losing our pregnancy and all the hopes and dreams that came along with it, as well as mending the rift that it caused between us.

We’ve had lots of great times and struggles over the last nine years. We learned how to be vulnerable and communicate with each other. The initial excitement of our relationship made way for deep love, care and respect for who the other person is and what we have together.

Therapy, coaching, attending classes, reading books and the intention to work on ourselves and our relationship really were necessary to bring us to where we are today. We have our motto, "Partners in Crime",on a small piece of art in our house and we really live up to it today after a lot of learning and growing.

"On a trip in 2016 hiking in Chile" Image supplied
"On a trip in 2016 hiking in Chile." Image supplied

And here is the kicker to the whole story.

Even though I don’t really believe in the institution of marriage and I don’t want any government or religion to be involved in my personal relationships, being married was key to getting us to where we are today. We fully love and support each other. We care for each other and still have a boatload of work to do in whatever is next — relationships are hard work. If we hadn’t been married, there would have been multiple times throughout the years where we would have split up and called it quits.

The lessons we were dealt, and dealt ourselves, felt more like a punch in the gut at times than a "lesson". So in some sense being married and the perceived societal pressures really helped us come together and work on our stuff so we could see it through.

Would I recommend getting married to anyone in their early 20s? Not at all. Because, you know, I had no idea what I wanted in my early 20s, and I think many other people don’t either. Pair that with the traditional concept of monogamous marriage for life, and I think you have a tough time succeeding.

However, was being married one of the key pieces of personal and interpersonal growth for me? Yes.

Did it make me a better man, her a better woman, and us together better partners? Totally. Do I expect it to be an easy ride from hereon out? Probably not.


Philip is a tech entrepreneur, maker, writer, and advisor. He lives in San Francisco and is the co-founder of cambyo, where he helps people develop their intimate lives. You can find him online at

This story was originally published on Medium, you can read the post here.