How do you get your boyfriend to propose? Some tips from Ali Wong and Jane Austen.

January 12, 2021
How do you get your boyfriend to propose?  Some tips from Ali Wong and Jane Austen.
Jose Llamas
Chai Tea with MilkNothing you can do by Ben Taylor

Dear Erica,

I’ve been with my boyfriend for 3 years now and I want to know how get him to propose. We’re definitely on the same page when it comes to long-term plans, but it just hasn’t translated into a real proposal. Any tips on how I can nudge him along?

Impatient in Ireland

Dear Impatient in Ireland,

I’d like to say that men know immediately when they meet the one(and yes, I mean You!). But more often than not, they are not as smart as we’d like and we must use certain techniques to get them to commit. Or as comedian Ali Wong explains, “A woman has to incept the idea into the man’s head. First passively and then if he doesn’t get the message, extremely aggressively. You gotta threaten to leave without ever actually leaving...”

I suggest you employ a number of Ali Wong’s strategies but with a deft, and dare I say, Jane Austen flair. Ali Wong jokes that she has spent the last ten years of her life making her husband’s lunches. And why would any woman in the 21st century do that? To make her seem indispensable. Now Anne Elliot might not have made Captain Wentworth’s lunches in Persuasion, but when tragedy strikes in Lyme, Anne’s cool head and intelligence remind him how indispensable she is in an emergency. He explains at the end of the novel that, “Her character was now fixed on his mind as perfection itself, maintaining the loveliest medium of fortitude and gentleness,” and adds that it was her behaviour “on the Cobb in Lyme and at Captain Harville's that had fixed her superiority” in his mind. She also showcases her fantastic mothering skills with her nephews which probably didn’t hurt.

The next thing you need to do is win over your future husband’s in-laws. Or at the very least make it clear you can handle his family’s brand of crazy. Because all families have their own brand of crazy. In Pride and Prejudice, Elizabeth Bennet not only wins the affection of his sister, who comes to adore Elizabeth, but also proves that she won’t be dominated by his bullying and snobby aunt, Catherine de Bourgh.

Now, while you don’t want to come across as too desperate, it is important that your boyfriend knows that you would say Yes! While I would argue that Caroline Bingley constantly praising Darcy on his “handwriting” was nauseating(to both the reader and Darcy himself), a man needs to know you would say Yes. After her brutal rejection of his first offer, Darcy only gets up the courage to ask Elizabeth a second time when he when he finds out from his aunt that Elizabeth would accept his proposal. As women, we are always nervous to seem desperate. But while it’s clear that men don’t like a woman throwing themselves at them, they also need to know that you are seriously interested. Rejection is scary for both men and women.

Now these are tried and true techniques of Austen heroines. If you are getting desperate, you can always go further. Ali Wong recognizes that desperate times call for desperate measures. There comes a point, she argues, “when you know that you’re too old and it’s too late to go back out there and find a new man and start the whole manipulation cycle all over again. So, you’re like, “I’m just gonna stick with this dude, focus on trapping this dude....” If you are getting that desperate, you can always pull a Rosamond Vinchley move. In George Eliot’s classic Middlemarch, Rosamond takes Ali Wong’s strategy of manipulation to a whole other level. A beautiful but ruthless blonde, she decides that the new doctor, Lydgate, is the only one who will do for her even though her family and friends advise her against the match. When Lydgate finds her in a flood of tears after a silly argument with her family, she pretends that her tears are because of him. And, despite his intentions not to marry, she pulls on his heartstrings and he instantly proposes. But, I suggest you be wary of anything too manipulative. As the unhappy marriage of Rosamond and Lydgate proves, it is not a strategy likely to result in wedded bliss.

Stick with Austen strategies. Prove you are indispensable. Prove that you can handle his family and relatives. And perfect the delicate balance of avoiding desperation while displaying interest. All tricky acts. But we women wouldn’t be as brilliant as we are if we couldn’t do all the above and far more...

Hope your wedding bells are ringing soon...