Dear Captain Awkward:

I (35F) have been with my boyfriend (36M) for sixteen months now. We met online and I moved with him after roughly two months. He has led me to believe that he would propose marriage in the time frame of two or three months. He told me this roughly six to eight months ago.

I have been annoyed and angry for the last two months. I love him, but if he is not ready to propose, then why am I here? I cannot ask him to marry me anymore then I could sprout wings and fly. I have given myself a pretty strict mental deadline. Past this date, I end the relationship and start looking for someone else. I love him. I admire him. He loves me. He is very wonderful, caring, and smart. It would devastate me to lose him, but I would hate myself if I stayed in a relationship that did not progress. I would hate knowing I pressured someone into proposing to me. I need to know that he wants to spend his life with me. Points that may not matter:

I know some people have a terrible time dating, but I had a lot of fun dating.

He pays for my health insurance and our last trip to visit his family.

I contribute financially and clean pretty much 95% of the time.

Our families love each of us and love the idea of us for each other.

There is pressure on both sides for us to marry soon.

Am I doing the right thing? I need to judge people on what they do and not what they say. My walk date is precariously close.

Thank you.

Confused and Sad

Dear Confused And Sad:

You say: “I cannot ask him to marry me anymore then I could sprout wings and fly.”

Why? I mean, sit with that. Why do you think that’s impossible for you?

Reasons I can come up with:

Expectations?

Cultural norms?

The way you were raised?

Traditions?

Gender expectations?

A lifetime of stories about relationships where they must progress to the next level or die?

Emotional stuff – wanting to be “chosen”, wanting to be sure of his commitment, wanting him to put himself out there and demonstrate all that to you?

Wanting to participate in those rituals – the proposal, a ring, the announcement, etc. – that are traditionally part of getting engaged for women?

None of the stuff in that list is stupid, or fake, or not real, and wanting it or feeling it doesn’t make you silly, or wrong, or a bad person or a bad woman – it’s giving you pause for a reason! It’s just the Stuff (patriarchy stuff, gender roles stuff, culture stuff)…that we grow up with and live with…and you can rebel against it or choose a different direction for your life but it’s still There, waiting for you, the second you relax your guard, reminding you that it would be really, really greeeeeeeaaaaaaaaaat if your life conformed to what was expected of you, that it would feel soooooooooooooo good to dance the steps of the dance you know, that your “reward” for waiting this out is just around the corner.

We don’t run ads anymore on the site but I’d almost like to turn them on for this post so we could see for ourselves how obscenely ready the world is to sell you on this particular dream. (True story: I Googled “baby gate” the other day, one time, b/c we’re thinking of getting kittens and need a way to keep them in one half of the house at night, and now the margins of my entire internet experience are 100% “CONGRATULATIONS U R HAVING A BAAAAAAAABY!” and it’s like “I’m not I promise you” and the retailers of the internet are united to say “HOLY CRAP, YOU’RE EXPECTING” and I’m like “I’m expecting…cats…maybe.” So then it’s 10% pet products and 90% “YOUR LITTLE BUNDLE OF JOY!!!! LOOK AT ALL THE EXPENSIVE STUFF YOU WILL NEED.”)

(One Google search, people. One.)

I got married in 2016 and what kind of dishonest shithead would I be if I tried to pretend that, while I loathed 99% of wedding planning, there weren’t times where it felt GREAT to be a bride, to be admired, to wear a pretty dress, to show off a pretty ring, to open lovely presents, to celebrate with friends and family, to be part of making a new family with my favorite person and to relax into being loved and chosen. Right now there is this weird double pressure where you’re supposed to both want the fancy wedding thing and also be SUPER OVER IT ALL that’s just exhausting. You’re an adult woman, you know what you want, you want what what you want, and that’s okay.

The problem is, Sad and Confused, is that the thing that you want and the exact way that you want it are on the verge of costing you the thing that you want. You are getting ready to walk away from someone you love! Forever! and that’s somehow less scary than saying, “Babe, I’m really ready to get married soon. Yes, to you, specifically. What do you think about that?” out loud and listening with an open heart and a cool head to whatever he says next.

And I think that’s really fucked up.

The stories/expectations/traditions that taught you that you have to silently wait for your own future to be revealed to you by some dude, or else you risk irrevocably startling the Adult Male into flight and must be forever alone are hurting you and your happiness.

Today, this 36-year-old man who shares a household with you, who is financially intertwined with you, who loves you and who has talked about marriage with you before, the one who asked you to move into his place with him more than a year ago either wants to marry you or he doesn’t. If he does want to marry you, and you asking him directly about this giant decision that will shape the rest of your future is so scary to him that it somehow makes him change his mind on that, then I call bullshit on him ever wanting it. People can get lazy or complacent, they can lie to themselves and other people about what they want, but someone who really loves you and plans to spend his life with you and who was truthful in the past about wanting that doesn’t suddenly go “Well shit, I wanted to marry you, but you mentioned marriage and that broke the spell, because you are a woman and I am a man, so, bye forever!”

If he doesn’t want to marry you, asking him about it and finding out will be such a relief, right? It will be painful, and expensive, but it will be a relief, also. You’re dying inside from the waiting, you’re prepared to leave the relationship if it’s not heading where you want it to. One conversation, and if it’s not going to work out you’ll know for sure that there was no saving it, there was no waiting it out, and every second you don’t stay is potentially wasted time that’s come back to you.

If you are not “allowed” to ask the person you plan to spend the rest of your life with questions about this, then, what are you doing? What is he doing? What is marriage for, if not connection and trust and vulnerability and loyalty and care? Are you gonna spend forever and have kids with someone who needs all major life events to be “LOL SURPRISE!”

I don’t have a way for you to bring this up with him without bringing it up. I have some thinking/writing/planning assignments and then a script for a conversation.

Stability. Imagine you find out soon that you are not ever going to marry this guy. What would you do differently with your money and your time, starting now? What would you do about housing and health insurance? Do you have your own savings that is not connected to him or the household at all? Make a Plan B for your own stability and financial well-being. You will feel more free and stable and confident if you have this plan. Daydreams. What are five daydreams you have about your future/your career/your education/your life that aren’t necessarily about getting or being married? Things you would want to do with or without this guy in your life? These things can be serious or fun, for example: “I want to be the boss at work, I want to become fluent in Arabic, I want to see the Northern Lights, I want to walk across my city on foot and take a photograph of everything yellow I come across, I want to do a pull-up, I want to write a poem, I want to learn calligraphy, I want to be a patron of the arts, I want a fat sweet dog that wears a little cape and follows me everywhere, I want to volunteer to serve people around an issue that’s important to me, I want to run for political office, I want to record video or audio of my grandmother telling stories of how she grew up, I want to be a beginner at something and an expert at something.” This list serves multiple purposes. You are an interesting person with a life and aspirations of your own. Companionship and love and family are important, but they are only part of the picture. Do you feel like the things on your list are within reach for you, the way your life is set up now? If you do marry this man, how will he help you do the things you really want to do? If you break up with this man, can this list will help steer you into what’s next? Reality. Are you happy now (aside from this tense-making worry about the future)? Do you like doing 95% of the cleaning? How did you decide on that division of responsibility? How have you and your partner tackled difficult conversations before? What are you most afraid of happening if you bring this up? Conversation. It’s okay to be uncomfortable or nervous about how to bring this up. He’ll probably be nervous, too, even if the feelings are compatible and the outcome is a happy one, because he’s dealing with the same collection of narratives and cultural expectations that you are, and the culture has given us so few stories about “We liked each other and then we loved each other and then we had a series of conversations where we mutually decided to get married and then we did” and so very many about “We just knew and then it was a magical surprise, no one ever had to talk about it, it all just materialized!”

So it’s okay to say “I feel really nervous bringing this up, but I want to talk about getting married. We talked about it early on, is that still something you want us to do? I really love you, and it’s something I want to do, so, can you let me in on your thoughts about this? Maybe we can figure out a timeline together?”

And then you listen to what he has to say. And you ask more questions. Are there reasons he hasn’t brought it up again before now? Are there particular things he’s nervous about? Is he feeling the family pressure, too? What’s he most excited about? Is he making sense? Do you feel safe and comfortable and like you can be vulnerable in this conversation? Are you on the same page about finances, living arrangements, kids/no kids, family stuff, etc.?

BTW if he’s pro the idea of getting married and wanting to put a plan together, you can say stuff in the conversation like “It’s important to me that at some point we do a proposal thing where you ask me, that tradition is really important to me.” Because if you want that and need that and look forward to that, it’s okay.

If he doesn’t want to marry you, I swear to you, I promise, it’s not because you asked him a question about it. It’s not because you upset some super secret plan he had, the petty way I sometimes felt when I was planning to sweep the floor but then I didn’t wanna anymore because my sorta bossy former roommate reminded me. Deciding to marry your favorite person is supposed to feel good and safe and like the other person has your back and wants to make it comfortable and easy for you. Wanting to know if the dude whose bathroom sink you’re scrubbing on the regular is into you That Way doesn’t make you “crazy,” “needy,” “clingy,” “pushy,” or any of the stereotypes that people try to attach to women who are a tiny bit assertive. If he treats you like “It was perfect, but you! You broke it with your questions!” then he was not someone who cares about your comfort and your dignity, i.e. not someone who would be a good partner in the long haul.

Letter Writer, I want you to have everything you want out of your life, including marriage with this guy if he also wants that. I want you to feel safe, relaxed, comfortable, happy, in love, loved, cherished, wanted, chosen, affirmed in your relationships. I think the way there is probably not a grudge-match with yourself or a Silent Loyal Girlfriend Secret Staring Match with him about how much waiting you can take. I think the way forward is probably a series of conversations, and I wish you all the best in having them.

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