L.A. Affairs: How I got my boyfriend to propose

Illustration of a couple happily jumping through a wedding ring.

By Annie Greenawalt

Aug. 15, 2020 7 AM PT

I was working at a commercial real estate company and dating a man who was married to his job and lacked a sense of fun. After two years of this, I told him I was going to venture out and start dating other people. He didn’t seem to mind.

About a week later, I met Rob. He was an attorney, worked in the same building I did and needed my help to acquire an access card. I thought nothing of our brief encounter until he left a note on my car with his work and mobile number, asking if I’d like to have lunch. The following Wednesday we walked to the nearby TGI Friday’s. I was impressed when he also ordered a healthy, oil-free, no-dressing lunch.

Another note on my car said, “Let’s have dinner so we have more time to talk.” I called him and explained that while I would enjoy dinner, I needed to be upfront: I was involved in a complicated relationship with my long-term boyfriend and had recently decided to date other men. Rob replied, “I respect you and him too much to intrude.”

So much for thinking I’d met my health match.

I was surprised when he called and asked me to dinner again, about a month later. By that time, I had broken up with the overworked boyfriend.

Rob lived in Los Angeles, and what I considered the “City of Cement” would soon become my stomping ground as we began dating. Over the next several months, all my weekends were spent enjoying some of the best that scenic Los Angeles had to offer. Hanging out at the Beverly Center, dinner at Moonshadows in Malibu, lunch at Gladstones, walking and shopping on Third Street Promenade and enjoying pedicures on Montana Avenue in Santa Monica. Rob introduced me to Mongolian barbecue in Westwood, where we stacked our bowls high with veggies, meat, noodles and stuffed sesame pocket bread with delicious morsels.

We discovered we both wore earplugs to bed. We both liked to exercise. We talked about how short life is and how one day is like a blip in the map of our lives. So it was never worth sweating the small stuff. Both of our fathers were short-fused and lacking in anger management, fueling our desire to stay calm and ride the waves that life brought us.

One evening we were hanging out on the Promenade and, as we walked back to our car, it wouldn’t start. Rob took my hand, walked to the closest bus stop and at 11:30 p.m. we were riding the city bus to his home. He held me close to his chest. It was at this moment I knew I had met a keeper. He showed me how protective he was. He cared about my safety. More important, he had encountered a challenging and frustrating situation, had come up with a solution and didn’t sport the kind of tantrum I’d seen in my father whenever he was faced with an inconvenience.

Months of dating turned into three years. And I decided to ask the question, “Where is this relationship going?”

He replied that he didn’t believe in the institution of marriage and proceeded to explain that a certificate or piece of paper wouldn’t change his love or commitment to me. “Why do women always want marriage?” he asked. I was stunned. I momentarily had no answer. I told him I needed time to think.

I was 27 and had never really thought about marriage before because I never met anyone I’d wanted to spend my life with before Rob. Could I stay with him if he didn’t want to be married? Not staying together would mean breaking up and heartache. For medical reasons, I knew I couldn’t have children. So, deep down, why did I want to get married?

I started journaling to help me navigate my complicated feelings about marriage and our future. As I tried to tackle this mountain of a question, I made two lists, side by side.

One list was titled “What women/I need” and the other, “What men need.”

Here is what my journaling deduced: Women/I need: (1) love, (2) to be wooed and romanced, (3) to be seen as beautiful in the eyes of their lover, (4) security — financial and in relationships. Men need: (1) respect, (2) sex, (3) to be affirmed, (4) to be appreciated, (5) the ability to protect and provide.

I presented the lists to Rob.

I explained I was getting everything I needed in our relationship, except for security. I needed him to tell our friends and families he was committed to me. And for me, that meant marriage. I asked him if he would stay with me if one of his needs wasn’t being met. He was silent. Then he stared into my eyes for one of the longest minutes of my life before saying, “No one has ever explained it to me that way. Thank you.”

About a week later, Rob was sizing my ring finger and shopping for a diamond.

The author is a personal and executive assistant to the chief executive of a multinational company headquartered in Irvine and has been married for 22 years.

Straight, gay, bisexual, transgender or nonbinary — L.A. Affairs chronicles the search for love in and around Los Angeles, and we want to hear your story. The story you tell has to be true, and you must allow your name to be published, We pay $300 for each essay we publish. Email us at [email protected]. You can find submission guidelines here.

The L.A. Affairs column is taking next week off and will resume Aug. 29.