On the Streets is a 91大神 weekly series about the chaos of modern dating: from situationships and endless talking stages,聽 to heartbreak and everything it means to be single in today鈥檚 world.
Justin* (29) has spent most of his dating life chasing women older than him. What started from a childhood crush slowly turned into a pattern that shaped his love life. But after one relationship left him stretched thin and heartbroken, he鈥檚 started to question if his type has been working against him all along.聽
What鈥檚 your current relationship status, and how do you feel about it?
I鈥檓 single, and my preferences have a lot to do with that. I鈥檓 drawn to older women, but it hasn鈥檛 really worked out for me. I鈥檓 trying to change because I know it鈥檚 affected my dating life.
I see. When did you first realise this preference?
When I was 11, I developed a crush on a 19-year-old family friend. She lived close by, and my mum would sometimes ask her to look after my siblings and me. It was obvious she preferred me to the rest of them. She always complimented my looks, and I confided in her more than anyone else.
Nothing inappropriate happened, but we were very close, and I held on to those feelings for a long time. Even after she left for university, we stayed in touch. We鈥檇 call each other, and she鈥檇 sometimes buy me gifts. I was too scared to tell her how I felt. We eventually drifted apart and that hurt, but I moved on.
At 15, I dated someone my age, but it didn鈥檛 last a term. In SS1, I got involved with a girl in SS3, and that was when I began suspecting I had a preference for older women.
Did you try to date within your age group in university?
I did, but it didn鈥檛 work out. I met Samiat* through my roommate, who had gone to the same secondary school as her. We became friends because she visited him often, and over time, I realised I liked her. We started dating in 2017.
It was a good relationship at first, but she relied on me too much. She expected me to think for her, even academically. She constantly asked for help with assignments and projects, and it drained me.
The effort wasn鈥檛 mutual. She didn鈥檛 show the same interest in my life or work. At some point, it stopped feeling like a relationship and started feeling one-sided. There wasn鈥檛 a defining moment that led to our breakup. I just got tired and ended things in our final year.
Did you meet anyone else after school?
Not immediately. I had a few talking stages, but even during NYSC, I found myself crushing on an older woman at work. I didn鈥檛 act on it. I stayed single until I met Esther* in 2022.
Tell me about Esther
We met at a club and danced together. There was instant chemistry. We talked on Instagram for weeks before exchanging numbers.
I was 25; she was 30. She hesitated when I told her my age, and I think that affected how seriously she took me. But I kept showing up for her. I was attentive and thoughtful until she eventually agreed to date me.
Nice. How did that relationship go?
It was good in many ways. We had a strong connection, but she kept parts of her life away from me. I never met her friends, and she was very private about her past.
It made me feel like she didn鈥檛 take me seriously. I kept trying to prove my maturity and that created pressure. There was also the financial gap. She was more established, while I was still struggling to land a good job after service. She never complained and sometimes helped, but I felt ashamed.
When she relocated to another state later that year, things got worse. I started to feel secondary. When I asked why she鈥檇 become distant, she said that I鈥檇 understand life better when I got older and climbed the ladder. Those words triggered me. We had a big argument , and it led to our breakup.
She apologised later, and we reconnected briefly, but it was the same pattern. After a few months, I walked away and blocked her.
That must have been hard.
It was. But a few months later, I met Ngozi* at a pop-up event. She sold beaded bags, and since I鈥檓 also creative, we bonded easily. We exchanged numbers, but she avoided me at first because she鈥檇 initially told me she was 30. She later admitted she was actually three years older.
Hmmm
I already knew she was older than me, so it didn鈥檛 matter. What I liked about her was how open she was. She鈥檇 just come out of a long-term relationship, so we stayed friends for a few months before dating.
But that relationship came with its own challenges. She needed constant reassurance and was very conscious of her age. The biggest issue, though, was that she wanted marriage soon.
Was that something you had remotely considered ?
No. I was 26 and barely surviving on a 200k salary. I didn鈥檛 feel ready, even though I might have tried for her. I just couldn鈥檛 give her a clear timeline.
The relationship became financially draining. I tried to meet her expectations by giving gifts and showing up, even when it stretched me. I didn鈥檛 want to feel babied, so I pushed myself. But deep down, I couldn鈥檛 imagine getting married in that state, and I knew my parents wouldn鈥檛 approve.
I kept stalling. She had always said she wanted marriage by 35, but the breakup still shocked me.
In October last year, she met someone else through church who was ready. I didn鈥檛 understand how she could walk away from a two-year relationship for someone new, but she was certain, so she ended our relationship.
I鈥檓 sorry. How did that make you feel?
I felt cheated. I was a wreck for the rest of the year. She eventually married him in January this year, and it鈥檚 been hard to process.
The past few months have been tough. I keep wondering if I set myself up for heartbreak. I can鈥檛 even fully blame her because I wasn’t at the stage she needed.
Now, I鈥檓 starting to accept what happened. Going forward, I鈥檒l be more cautious. It would take someone who genuinely wants me and understands me for me to try again with an older woman.
That sounds fair. How have your experiences shaped your idea of love and relationships?
I鈥檝e learnt not to pressure myself to meet someone else鈥檚 expectations, especially financially. I stretched myself too much in that last relationship. I almost went into fraud because of how desperate I was to meet her demands.
I鈥檝e also realised how important timing is. Being at the same stage of life matters more than I thought.
Finally, how are the streets treating you? Rate it on a scale of 1 to 10.
4/10. I don鈥檛 enjoy being single. Maybe it鈥檚 because I鈥檓 still hurting from my last relationship. I hope to feel better about it once I get to a better place emotionally.
Read Next: I Became My Boyfriend鈥檚 Boss, and It Ruined Our Relationship
