Love Letters

I’m the Oprah of dating advice, but haven’t ever had a relationship

I’m good at helping friends through their relationship dilemmas. I’m not good at finding romance for myself.

I am a 22-year-old art student. In my group of friends, I am known as the Oprah or Dr. Phil because I give good advice. I help my friends with their love lives, but I haven’t been in a “relationship” since the fifth grade. I’ve had depression and anxiety since I was 15, which gets in the way of my confidence. Sometimes I feel tied down with a ball and chain strapped to my ankle. Whenever I find the confidence to talk to a guy I like, I feel stuck.


I want to avoid online dating; I’ve always wanted to meet a guy in a library or a coffee shop. Recently, I went on a lunch date with a friend of a friend, but I wasn’t interested in a second date. I spend a lot of time fantasizing about a perfect boyfriend: We travel the world with our friends and make each other’s lives more colorful. I don’t mind being single. But how much longer am I going to be alone? What should this depressed girl do?

— Alone

A. First, make sure you’re getting the treatment you need. I assume you’re in therapy/have a doctor for depression and anxiety, but if not, seek help. Self care is the most important thing.

Moving on to the dating. Please know that with that one mediocre lunch date, you proved that you can do it. You had a meal with someone, decided you didn’t like them enough to see them again, and then moved on. That’s like . . . 99 percent of the dating experience. Please give yourself credit for making it happen.

Also know that many single people would love to find romance in a coffee shop or library. But it’s a busy world — and those romantic meetings aren’t as perfect as they look in the movies. If you start talking to someone at the library, you have to decode that person’s intentions. On an app, you can assume (to some extent) that the people you meet have signed up to date. My advice? Have first dates in all of those lovely places. Tell the people you meet on apps that you’d like to get together at a coffee shop, the library, etc. Then you get to live the fantasy.


No matter what, try not to label yourself as “the friend who gives advice but never dates.” Sometimes when we make sweeping generalizations about our romantic lives, we make all of the negative things come true — whether we want to or not. You are someone who wants — and is capable of — finding love. You just don’t know when it’s going to happen.

— Meredith


Stop telling yourself that you don’t mind being single. Obviously you do, and that’s OK. ROADRUNNER

Your depression does not doom you to being alone or unhappy. But your grossly unrealistic expectations of what a relationship is most certainly will. THATGUYINRI

I was also the person who “gives advice but never dates.” I was always waiting to meet a special person in my normal (nerdy) activities or at work, but it didn’t happen. When I turned 30, I realized that my past strategy [wasn’t working]. So I went on dating sites. Three years later, I went on yet another routine coffee date. And it was fantastic. We got married a year later. CHASINGPAPER


Meredith Goldstein is in her ninth year of writing Love Letters for The Boston Globe.