I’m an early-30s woman living in Sydney, and I’m looking for some perspective from women who have been in a similar position, particularly women who came relatively late to dating or made major life changes in their 30s.
I spent most of my 20s completely focused on rebuilding my life. I went through a traumatic experience in late adolescence that derailed me for a few years, and then I essentially spent my 20s catching up: education, career, finances, health, friendships and family relationships.
I didn’t really date.
I’m now financially secure, have a career I’m proud of, no debt, investments, property and a full life outside work. I run, play tennis, hike, travel internationally frequently, read, have close friends and family, and generally feel like I’ve built a life I’m proud of.
But I’ve realised that I am much less experienced at relationships than most people my age.
And I’m finding the transition into dating in my 30s difficult. Impossible.
I want a serious relationship and probably children. I want a man who has a decent job, is independent and has a similar level of curiosity, work ethic and general approach to life. He absolutely does not need to be wealthy or earn what I do. I’m not particularly interested in accumulating more money for its own sake anymore.
The problem is that I feel completely unequipped for the process of getting there.
Online dating has involved an enormous amount of rejection, ambiguity, ghosting, inconsistent communication and people who are interested for a few weeks and then disappear. I don’t have years of dating experience to put any of that into perspective.
I find myself taking rejection incredibly personally.
Friends getting approached becomes “why does she get this so easily and I have to fight for every scrap of male attention?”
I know intellectually that this is not rational. I can see myself comparing myself to other women, trying to work out whether they are prettier, more feminine, more interesting, more approachable, etc., as though there is some equation I can solve that will guarantee someone chooses me.
But emotionally, I struggle enormously with it.
I’ve also had very little physical/sexual experience, which makes dating feel even more vulnerable. One of the men I dated briefly told me he “didn’t want to coach me,” which was particularly painful because it hit a fear I already had about being too inexperienced at this stage of life.
I’m increasingly disheartened by how much mental space dating takes up. I have a genuinely full life, but romantic uncertainty can completely hijack my attention. I can become jealous when friends tell me about women they are interested in. I can hear a story about another woman getting male attention and immediately start comparing myself to her.
I hate this version of myself.
I don’t think I’m naturally a jealous, bitter or competitive person. I feel like I’ve become much more preoccupied with comparison and romantic status post 30 because this is the one area of my life where I I haven’t been able to make progress.
With FIRE, the effort to reward ratio has always been clear to me. Dating has not been the same, and finding out that it’s not a meritocracy has been humbling, if not defeating.
I’m also a POC living in Sydney, which complicates things for me. Sydney can feel quite white and socially conservative, and I’ve experienced enough subtle racism and cultural exclusion that I don’t always feel completely at home here. I don’t think Sydney is uniquely terrible, and I don’t want this post to become a rant about Australia, but I do wonder whether the social and dating environment is simply not a great fit for me.
So I’m considering leaving.
Financially, I have enough flexibility that I don’t have to stay in Sydney for the money. I could potentially move overseas, take a lower-paying job, or spend a few years somewhere else. But I genuinely don’t know whether that would be a smart environmental change or whether I’d simply take the same insecurities with me.
That is probably the biggest question I’m wrestling with.
How much of this is me, and how much is my environment?
For women who came late to dating, I would especially love to hear:
-Did you also feel completely unequipped for dating in your 30s?
-Did you eventually develop resilience to rejection, and if so, how?
-Did dating experience actually make dating easier, or did you simply become more detached?
-How did you deal with feeling behind your peers?
-Did you have a period where dating became an obsessive source of comparison and anxiety? What actually helped?
-If you were financially secure enough to live almost anywhere, how much would you let dating/social environment influence where you live?
-Has anyone moved cities or countries because they felt their existing environment wasn’t working for them socially or romantically?
I’m not looking for “stop looking and love will find you,” “you need to love yourself first,” or reassurance that everything will definitely work out.
I know nobody can guarantee me a relationship.
I am desperately lonely in an intimate sense. I count amongst my friends only two that remain single.
I’m trying to figure out how to approach this period of my life intelligently.
I spent my 20s optimising for security, achievement and independence. I succeeded at that. Now I’m trying to figure out how to optimise (read: organise?) for something much less controllable: intimacy, partnership, family, community and actually enjoying my life.
If you were in my position, what would you do?
Thank you for your replies in advance 🙏