Ask Olive

How do I get the intimacy I crave when my partners keep disappearing?

Hi Olive,

I’m a 36-year-old single woman who is starting to lose hope that I will find sustainable love with anyone.

Five years ago, my boyfriend of four years left suddenly with no real explanation. We had very much been in love and had a genuine, deep friendship — or so I thought. He later explained it was a crippling fear of closeness that sent him running. Knowing this didn’t lessen the devastation, and for a long time, it made me question my sense of reality and my worth.

I was still optimistic after I recovered that once I started…


Ask Olive

My life doesn’t feel like my own

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Dear Olive,

Recently I’ve felt like my entire life is not my own.

I’m doing the things that I’m supposed to do, receiving positive feedback, and generally living the life that I always thought I wanted. But now that it’s here and I’ve actually been living it, it feels like it doesn’t belong to me. It feels like I am going through the motions of being successful or being “happy,” but something always feels off.

I am 22 years old, interning in New York City for the summer. In a couple weeks I’ll be ending my internship and going back…


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Advice for those who want it

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Dear Olive,

In recent weeks, I’ve come to a sad realization about my life. I’ve spent years of it chasing praise for everything I do. When I don’t get it, I tend to act out in negative fashion, thinking “someone’s going to notice my actions,” but all it does is piss everyone off and further compound the situation that I’m in. My sense of self-worth has become dependent solely on the accomplishments I’ve done, in order to prove to people that I’m doing something with my life.

The chase of praise goes back to one particular moment in my life…


Ask Olive

Advice for those who want it

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Dear Olive,

It’s a classic story of girl meets boy and has an amazing six-month relationship (I know, only six, why am I still hurting? Maybe it’s a mid-life crisis, since I’m 30?). It started off freaking amazing, with love bombardments — meeting his parents on New Year’s Eve, flying off on vacation on my birthday, having amazing first dates with lovely stories and funny moments, sharing a love for sports, lovely gifts, making a Christmas tree together… Moments that I have never had before.

But during this time we also had some big fights. Like his disappointment when I…


Ask Olive

Advice for those who want it

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Dear Olive,

I read the letter from “Trapped in My Fears and Constant Self-Doubt,” a 19-year-old, with great interest, as I feel the same way… but I’m a man in my mid 30s, married with kids, and on my second career! I also feel trapped, in two ways: When I was that age, I listened to one kind of fear and chose to go down the route of getting a corporate job, which even as I was studying for it I knew wasn’t right for me — like it was sucking the life out of me. …


Ask Olive

Advice for those who want it

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Dear Olive,

I met a guy traveling and don’t know what to do.

I’ll give you the short version of my problem:

I met a guy while traveling in Europe. We ended up living and co-working together for four weeks and had the most incredible time together. We both knew our time was coming to an end, as I had plans to travel on and he had to move to San Francisco for work. We kept in touch every day and he invited me to visit him in San Francisco when he moved there. After two months apart, I flew…


Ask Olive

Advice for those who want it

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Dear Olive,

I met my wife 20 years ago, in high school, and we have two kids. Five years ago while I was more focused on my work than I was on her, she met someone and has been cheating on me with this man since. I discovered this three years ago. First I wanted to leave, but I didn’t feel able. She didn’t want to leave either, she just wanted to live with me as a roommate and keep seeing that man.

I have never accepted this. At the time I didn’t know that she’d been in love with…


Ask Olive

Advice for those who want it

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Olive, I’m becoming a dangerous recluse. What should I do to deter this? I’m a single, 42-year-old female. I’m an only child, I’ve never been married, I have no kids, and I’m an elementary school teacher of 17 years. I just gave up the last bit of identity I had, to move in with my mom for financial reasons. I’ve got superhuman abilities to fake who I really am professionally and personally. I’m intelligent, pretty, and I’m the life of the party that everyone wants to be around, yet I don’t want to be a part of the party anymore…


Ask Olive

Advice for those who want it

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Dear Olive,

I’m part of a work culture that is highly toxic. I get paid well, so until recently I hadn’t thought of moving on. But last month, my boss promoted my colleague, and so now I report to him. The promotion as such doesn’t bother me. But the arbitrary nature of making him a boss, when he is less qualified than I am and has less experience, hurts. I feel the weight of humiliation everyday when I wake up.

I am also a single woman who finds validation from her workplace. I used to think that I could shut…


Ask Olive

Advice for those who want it

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Dear Olive,

For most of my life I’ve stayed in my shell because it feels safe. But now I’ve come to a point in my life where I have to make decisions for my future. I can’t hide from the inevitable any longer. I’m 19, and whether I want to or not, I have to face reality. But I can’t help but feel afraid, unsure and insecure about what is best for me and what choices to make. At times it feels so overwhelming that I feel hopeless, and I question how can I survive or even live in this…

Ask Olive

Advice for those who want it Askoliveforhelp@gmail.com

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