Dating In Your 30s — Is It As Bad As It Seems?

May 29, 2025 by Andrew Small No Comments

Dating in your 30s in Los Angeles (or any big city, really) is the pits. Unique to an arts city like L.A., however, is the bustling beehive of attractive people trying to be an actor, singer, pro-wrestler, whatever. Sooner than later, you realize that meaningful dating is sometimes the last thing people want to be doing. And if you’re a woman who wants to settle down and have a baby, Los Angeles can be among the worst places to secure your future, ahem, date. How do you know for sure if you’re a placeholder until your crush makes it big as a hotshot lawyer, Beverly Hills dermatologist, reality star… Or if they’re actually somebody to invest time in?

Here are a few tips to avoid getting stung right in the kisser!

Many women in their 30s find themselves pretending to want less from a relationship than they actually do. Around 28, I began dating men again after a nearly nine year hiatus. I never believed I was totally lesbian, but I hadn’t had intercourse with a man since I was 19.

I took it slow, rolling in the New Year with a six-week fuck fest with an Irish banker who once drunkenly fell asleep while he was going down on me. Suffice it to say that never happened with one of my lesbian lovers! Still, I was tipsy on my growing attraction to men and followed it like a buzzing bar sign.

My second male lover was a mega-rich venture capitalist embroiled in a custody battle with a mistress, all while maintaining a family on the East Coast. I found this out during our tryst, which lasted brief one-and-a-half months.

Around this time, I met the man who would be my longest relationship with a penis in almost a decade. “Jimmy” and I met at a book signing and he talked my head off before asking for my number outside Book Soup in Hollywood. He wore dirty jeans and a thrift store shirt and was at least ten years older than me, if not more. He reminded me of a drunk in a Charles Bukowski novel on one of his sober days. He turned out to be a bit of a narcissist but he was kind and went down on me often (staying awake the whole time!). After seven months, what he didn’t do was EVER put a photo of me on social media.

His online photo albums were littered with photos of himself in his glory days. Straddling a motorcycle. Beaming a mile-wide smile at his old ad job. Fishing. Skiing. Meeting the president. Not one photo of us broke up the “perennial bachelor” version of his life that he showed the world.

Dating Tip 1

One of the first hard and fast rules of dating in the new millennium is paying attention to the parade of photos your flame rolls out on Instagram and other social media.

What version of themselves do they want the world to see? In my experience, if it’s an overly sexualized one, then they may be hungry for validation from strangers and could have a hard time with monogamy. If they’re always drinking or drugging or holding a gun for that matter, you may have cause to worry. If they have a decent mix of family photos, office picnics and a few nightclub snaps, then you probably have a non-sociopathic, somewhat grounded potential mate. Congrats!

My brother used to tell me there are two kinds of guys out there. “Sex guys” and “sex and more” guys. It was my job to discover which one they were before they broke my heart.

As I mentioned, around 30, I began thinking about my future with a man. This future inevitably involved a child. Given I was fairly new to the dating game with men, I made a lion’s share of mistakes, which, lucky for you, I’m open to sharing! What I did right, however, was read a lot of books about relationships and even went to seminars and weekend retreats where I learned how to ask for what I need in a way that men could understand.

While dining at Café Gratitude one evening with a girlfriend, a brave waiter walked up to me and commented that while he wasn’t my server, he couldn’t help but approach me and tell me I was beautiful. I was flattered and thanked him. I gave my friend “the look” which asked, “Is he cute?” She nodded. The guy sort of hid behind a beam, embarrassed suddenly by his bravado. I read him as sweetly honest. But at that time my picker was shit. He did get my number that night and we would date for two weeks before he broke it off. (The day before Valentine’s Day. Which I spent with that same girlfriend at a downtown art show, because the waiter didn’t “believe in” Valentine’s Day.)

He begged me back after a week apart; we slept together and were back in the saddle again.

We did all the stuff a normal couple does: kiss lots in parked cars, have breakfast at diners and people watch, buy Plan B. After a few weeks of this, during dinner, I broached the topic of my future. I told him that in 3-5 years I wanted to marry and have a child. He looked mystified. He said he had zero plans and zero savings to support my desire.

Most women would freak out, back pedal and instantly regret being as honest as I was. But the most striking difference between my 20-something self and my 30-something self is that I felt no fear. I had been supporting myself financially for a while now. I had been happily single for a few years. I was the woman I had aspired to be and wasn’t sure I’d ever have the strength to become.

I thanked him.

Dating Tip 2

He made me think harder about who I was looking for versus who I was attracting. I started writing about, in detail, the sort of person I wanted to invite into my life and began prioritizing those qualities. For example, I knew I wanted a child, but what kind of father did I want for her? I knew I wanted a non-judgmental person, so why wasn’t I more discerning about who I shared my life with? I needed somebody who had sewn his wild oats (and was totally OK that I had sewn mine too!) and who was ready to commit to me. I needed somebody I could feel like myself with and that who I am is more than enough.

Men tell you who they are and they tell you right away.

Listen to men because they are more honest than women about their identity. In fact, if I had taken to heart the man he presented early on, I would have never cast him as anything more than a “sex guy.”

There were a few others that cropped up before I met my fiancé. Including the 24-year-old who routinely asked if he could expect a BJ at the end of the date. And some sweet ones too, like the 55-year-old casting director who I was trying on like a vintage coat but whose sincerity forced me to confront my own truths: how committed was I to finding who I was looking for, really?

Dating Tip 3

The sooner you nail down your inner truths, deepest desires AND are willing to go to bat for yourself, the faster those things will be delivered to you because you will seek them out, work for them, or in the least, recognize them when they appear.

After dating awhile it can feel like you have a wardrobe closet full of ever-ready personalities to pick from depending on who you’re dating and who you think their fantasy girl is.

Dating is hard, but dating while lying is harder. Keeping track of false personas is a lot of work and it leaves you feeling drained. Know thy self and be true to her.

Dating Tip 4

The last and most important rule: If you pretend to be somebody else and you get the partner you lust after, you will be pretending for a lifetime. If you’re honest about who you are, you will weed out the wrong candidates and find your perfect match!