September 20, 2023

6 Things to Consider Before Asking your Best Friend to Marry You.

I had never been proposed to before, so I really didn’t know how to handle it.

At 42 years old, you think I’d know but I wasn’t prepared for it.

My first marriage was a mutual agreement to start our lives together when I was 21 years old. It was scary but exciting, and I was definitely up for that kind of adventure.

This time around, it caught me off guard. Although I had mentioned that I saw myself being married again one day, I never actually meant that he should ask me to marry him. And after our third breakup in four years, I figured we are both moving on.

So when he asked me out for lunch at a fancy restaurant one day, I didn’t think that it would lead to him proposing just a month later. I went to find out how he was doing. I had no ulterior motives and never did I think we’d be dating again.

He was 10 years my senior, and I felt that we are at different stages in our lives so being friends might be the better option for us. I still cared about him and was happy to meet him but I was a little apprehensive because I hadn’t heard a peep from him in months.

I decided to go with the flow when I accepted his invite to stay at an Airbnb in a wooded area close to a town. The place was inconspicuous on the outside but meticulously kept inside.

A large fireplace with a wide, sleek, light-colored couch in front, and a fancy kitchen with a small bar, perfect for hanging out and having a glass of wine. A gorgeous bedroom with a walk-in bathroom, rain shower and beautiful sleek counters, soft beige towels and a walk out to the back yard with a gently flowing river. It had a small table and chair set, perfect for sitting and observing wildlife while sipping coffee (or a replacement, as I had quit coffee at that time) and listening to the water.

I felt caught in a beautiful fairy tale, whisked away by a man I still had feelings for. (Rest assured, though, I slept on the sleek couch and not in the bedroom—I wasn’t gonna make it that easy for him.)

When he asked me to marry him a month later near the longest, sweet-water beach in the world, with the sun setting behind him, he went down on one knee and told me that I was his best friend and he wanted to spend his life with me. I kept asking if he was serious, because a part of me doubted he was.

But then I saw the tears in his eyes. So, I said yes.

In hindsight, I realize that I didn’t want to ruin such a beautiful moment. And I really wanted this to be real for us. I wanted us to have that fairy tale story. If you don’t know me personally, you don’t know how much of a fairy tale fan I once was.

However, now I see how I may have sabotaged myself unknowingly. Because this fairy tale life and proposal was not realistic. There were things we needed to discuss before we made the decision to get married, especially, at our age. We weren’t starting out with nothing like when we were 20 years old.

I knew the day would eventually come when we’d have to discuss the details of our marriage. However, that day never came. Instead, I found myself on a night out asking him how he envisioned our marriage, not just the wedding celebration but how we would spend our lives together.

He tried to avoid the talk and told me that we would just figure things out when it was time. That answer left me in limbo.

A couple more months went by and I began to have doubts that we would ever work out. Until one day when it became clear that our relationship wasn’t working. We rarely saw each other because I had to work so much. Inflation had hit, mortgage rates were up, and my company lost a few employees, which left me and the rest of my coworkers to pick up the shifts that could no longer be covered.

My partner also took on a new job, and did I tell you he lives three hours away? So we rarely saw each other and it became harder and harder to contact him. I often had to send him a text requesting that he call me, otherwise he rarely would.

Our situation put more strain on our relationship, and I began to wonder why he even wanted to get married in the first place. I started to doubt that it was because he wanted to spend his life with me but because he was afraid of losing me as a friend or having to see me get married to someone else one day.

I didn’t understand anymore why he asked me. And I also began to doubt my own decision to say yes.

Then one day, there was a confrontation and we clashed on multiple issues. We stopped speaking for a while, until one day I received a long text message from him. To make a long story short, we decided to not get married.

I’m sharing my story of almost getting married to my best friend to help others understand the foundation of any good proposal—and good marriage:

1. Propose after you’ve discussed what marriage will look like, so you don’t put your partner on the spot where they can’t make an informed decision. Have a plan about finances, living arrangements, and approximately by when you want to be married.

2. For some people, it’s customary to talk to your partner’s parents before asking. Others choose to speak to a lawyer or a therapist beforehand. Marriage is a big life change and it’s important for you and your partner to be informed and get advice.

3. Know that love is not all you need to make a marriage work, because if there are other important issues that don’t work, love will dissolve. You also need respect, honor, care, financial stability, similar values, an understanding of equality and equanimity in relationships, and hopes and dreams for the future that are aligned.

4. Discuss parenting styles, especially if you have children from previous relationships. Be clear that each parent is responsible for their own children and that neither has the right to control the others way of parenting.

5. Understand that getting married and living your lives together does not mean that you have the right to make decisions for your partner. Each of us is our own person, and should be trusted to make our own choices when it comes to things like birth control, parenting skills, occupation, and how we spend our free time.

6. Know that each person has a right to respectful treatment, personal space, freedom to express how they feel, and a right to be heard. Marriage doesn’t mean that we own our partner.

Marriage can be a wonderful thing—I had many beautiful years with my ex-husband. There will always be issues in relationships but with an open mind and heart, we can discuss anything and make changes that work for both parties.

I still believe in marriage, but no longer seek it out. I know it will happen if it’s meant to.


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