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Dating Advice from a Woman Who's Been Proposed to Nine Times

The woman is my mom.

Claire Sullivan

Illustration av Ashley Goodall

I'm 25 and single. I've had plenty of boyfriends, but now I'm alone again and striving for that same thing I've been looking for since I was 15. Independence, self-worth, and someone to wrap myself around at night when it's so cold that I can see my breath hovering above me in bed.

I remember going on a date with this short English guy when I was 18. We ended up back at his place where he lit candles, poured us glasses of red wine, and played Joanna Newsom from his shitty laptop while we had sex. It was gross. This might sound like a weird litmus test, but I doubt my mom would've slept with the English guy if she were in the same situation. She's smarter than me. She would have seen the candles and known what a hazard they are and left. She would have been comfortable with the knowledge that she didn't have to sleep with him to make herself feel fulfilled.

I know this because my mom has been proposed to by nine different men in her life. She only married one of them—my dad—and they're still together today. Beyond her love life, though, my mom is just one of the most content people I know. Sometimes I think I could be happy in life if I had the self-worth to turn down so many offers from guys.

So I called up my mom to find out how she seemingly never worried about dying alone.

VICE: Hey, Mom, I think you're great. But tell the people a little bit about yourself. Would you describe yourself as a feminist?
Of course, I'm a feminist. I'm a feminist from the second wave and the baby boomer generation, but with intersectional views. I'm a child psychologist with my honors in psychology and masters in education from the University of Tasmania.

I wanted to talk with you because sometimes I feel like I need to be in a relationship to be happy. What do you think about that idea?
Oh, I think that's crazy. Relationships are a kind of add-on. Unless you're happy with yourself, a relationship won't make you happy. I've often seen very young women trying to make their relationships permanent. They're trying to find their meaning in life from another person, rather than trying to find meaning within their own interests.

You seem to be suggesting independence is important.
It's very important. And I think the less independent you are in your 20s, the more likely you are to end up in a relationship where you're the one making all the compromises.

Yes, well that's easy to say when nine guys threw themselves at you. Do you think it was your independence that people found so charismatic?
Maybe. I used to have this dark red hair that you only ever hear about in romance novels. My friends used to say, "You've always got someone hanging around and dangling off your finger." And I suppose I did. But it was mostly because I did favor my independence, and that I wasn't desperate to meet someone.

I used to say, "Oh, I'd really like to meet someone," and then I'd see men without teeth, with messy hair, overweight, and stinking of cigarettes, and I'd think, I'll just stick to the cat. I'm quite happy to share my bed with the cat. He'll keep me much happier.

Let's talk about these nine proposals. Can you walk me through them?
Well, I said yes to three but only married your dad. And the first person actually didn't propose. He actually told me that his mom had told him to propose... then 30 years later, he came out as gay after his mom died. We were good friends, but, yeah, nothing much ever happened. We kissed in church sometimes.

Readers might think the church thing doesn't seem to fit in the rest of your life. Have you always been Catholic?
Yes, but for a while, I was thinking about joining the Anglican Church. Also, I went out with an Anglican priest. He didn't propose, but he did end up in prison.

Who was the next guy to propose?
The one after that I actually said no to. We were in our last year of college. I wasn't sure he was the right person. He had quite a temper, which made me nervous, so I said no. I broke his heart. I was horrible to him. Out of all the hearts I've broken, his was the worst.

The next one that proposed was an African man; he said God had told him to marry me. To which I said, "Well, that's funny, because God didn't tell me to marry you, so I don't think it's really going to work out." He was too fundamentalist and didn't have room for my feminist views.

The next one, he was as drunk when he asked, and I said, "Well, ask me tomorrow when you're sober, and I might think about it." He was lovely, but we were friends. You know, that's all. We really were just friends.

And the next one I said yes to. I was about 35, and his name was Ned. He proposed—this is terrible—but he proposed in a crossword. Weird. And then he knelt down and asked me, I said: "Yeah, OK." And then about three months later he changed his mind. Like as though he just woke up and decided to switch from oatmeal to cereal for breakfast.

The last man to propose before your dad, I said yes to, and we were officially engaged, but he was hard work. I went with him to volunteer in a psychiatric hospital in London. He told me at the end of the trip that the relationship wouldn't work out. I just wished he'd said that before I spent all that money, and had such a horrible time.

How did you know it was right with Dad?
I'd only known Adrian a week before he said, "I think we should get married." I said, "Yeah, it seems like a logical thing to do." Well, it just felt like I'd known him forever because we had so much in common.

What have you learned from relationships and marriage?
Steve Biddulph [a parenting educator, author, and psychologist] says there's got to be an attraction between "two heads, two hearts, and two sets of genitals." And all three are pretty important for a successful relationship, I think. Because if you really care for someone, but their values are atrociously different to yours, then it will just cause problems.

I was reading Germaine Greer [an Australian feminist writer] when I was in college. Feminism was new and exciting then, and I refused to shave my legs to please guys. I also became a pacifist, which fitted in well with my feminism. I had a lovely friend who was an older feminist in Launceston, Australia, and she used to say that being a feminist doesn't mean excluding love; it just meant finding the right partner who accepted equality.

I've learned that if you're the right couple with the right attitude, and if you're prepared to communicate, then it'll work. It's also important to not have any fear in a relationship. You have to be friends.

I'd like to find a partner who is also my friend.
Yes but don't panic. I didn't meet Adrian until I was 38, and we still had a family. We still had a lot of good times, and we're still having good times. There's no rush. I'm glad I didn't marry any of the others; I think going through a divorce would be just horrible. I have a lot of trust in myself, yeah, that's part of it—trusting you're making the right decisions. We are all much happier if we focus on never denying ourselves and our values. But this gets easier as we get older.

Do you have any advice for heartbreak? Everyone just says, "It just takes time."
Yeah, just be kind to yourself and take your time. And know that you'll get over it. Cry when you want to. Write [your ex] a letter and say how mean and terrible they are and then rip it up.

Maybe getting proposed to was just way more common when you were growing up, though. Were people asking all your friends to marry them too?
No, none of my friends got proposed to as much as I did. No. I'd forgotten I was a bit of a femme fatale.

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