Dating and Relationship Advice

It's tough to say no — especially to your best friend.

It's even harder when you two have grown up together, spending the last decade traipsing around your neighborhood, hitting up the local 7/11 for slices of midnight pizza.

When quarantine hit, we could no longer wander around together, arm in arm, spilling our latest boy troubles.

I haven't seen her in person since the lockdown began. Our friendship, once defined by a quick call and a meet-up minutes later, became an endless exchange of iMessages.

In recent weeks, that exchange has evolved into a dumping ground for texts announcing her heartbreak. She — we can call her Lilly — had spent months in a rocky relationship with a guy who never took her or her feelings seriously.

In those months, as her relationship with the guy transformed, so too did the bond between us. She became dependent on me for support and words of encouragement. She lost track of her goals, and her excitement and energy for her work faded away.

I became her soothsayer, prophesying whether the guy — we'll call him Dominic — cared for her or not based on the one-worded texts she received from him.

This turned into barrages of text messages.

I'm going crazy.

I can't live without him.

I have to apologize to him.

She knew that she wanted a relationship he would not provide her. I knew she knew this because she told me many times. But in those moments, she feared the potential of losing him and starting over so much that she seemed to gloss over everything she hated about him for the minute chance at renewing their relationship.  

Over the course of months, she began to justify his negligence, telling me he changed and that he promised he'd do better. I must have heard this fable at least 10 times in eight weeks. It pained me that she always believed it.

And each time, the texts were overwhelming. They sounded desperate, like Lilly would do something unthinkable or was slipping into a depression brought on by the realization that the man she loves does not love her in the same way.

Her texts were cries for help. They were filled with sorrow and uncertainty. For months, I diligently responded, crafting my texts to Lilly carefully and cheerily.

You can do this.

You're strong and capable, and you don't need Dominic.

You are whole, and you have a full life that deserves your attention.

I thought I was being a good friend by being there for her. But as months went by, and I continued sending these messages, I realized my words could not help her.

Our friendship had transformed into therapy sessions, where she would spend hours venting about her feelings and I'd be on the receiving end, unsure of how to respond or whether it was even responsible to. Lilly seemed to expect me to provide counseling, something I have no confidence, certification or credibility in.

There were so many times I didn't feel qualified to say anything, so many times when I worried my words would push her in a bad direction.

These feelings stayed with me for a while, even after Lilly and I talked about boundaries and how overwhelmed I felt. I feel guilty about telling Lilly I couldn't handle what she was throwing at me. Isn't that the job of a best friend? I wondered.

Some of our conversations are drier now, as if we're both holding back the layers of deep feelings we used to share so easily around each other. We're still laughing about the absurd things we come across — memories of our childhood and hilarious memes. But when the conversation turns to dating, it feels as if a third party has entered our conversation: restraint.

Some days I question whether telling her that therapy isn't in my job description was the right thing to do.

I still am not sure how far the job of a best friend extends. Just like Lilly, I too am spending some time reflecting on relationships and how they work. I don't have answers right now, but I hope one day I will.