by Niall Doherty

My first romantic relationship happened back in 2004. I was 22 years old, spending six months working at a ski resort in Vermont, USA. I was just beginning to overcome my crippling shyness, and was delighted to find myself in a relationship with a beautiful Brazilian lady six years my senior. Let’s call her Izabel.

We both fell deep into the relationship and ended up living together for the final four of those six months. But there was trouble up ahead. Neither of us had an American green card. We couldn’t stay in Vermont forever. What would we do when May came and the ski resort shut down for the Summer? Would we figure out a way to stay together, or would we break up?

Long before May came, I had already made my decision. I wanted to go my own way after Vermont.

But I was scared to tell Izabel. She knew we needed to have that conversation, and even tried to start it a few times, but I resisted. I didn’t have the guts to tell her what would become of us. Neither did I flat-out lie to her or make any empty promises, but it was still a cowardly route I took.

Never having that conversation was very tough on Izabel. For her, there was no closure to the relationship. I returned to Ireland and started anew, diving back into college and getting on with my life. She stayed in the US and wondered if she still had a boyfriend. She would call me up every so often. I could hear the hurt and disappointment in her voice as she gradually came to accept that we were finished. She ended up resenting me and my cowardice for a while. I couldn’t blame her.

If I could do it all again

I was going to hurt Izabel either way. I didn’t want the relationship to continue beyond Vermont. We were destined to break up no matter what.

But I could have handled the whole situation much better. I could have lessened the hurt I caused.

If I could go back and live those final months again, I’d make myself sit down and tell her everything. We probably would have needed multiple sessions to talk everything out, and I know such conversations wouldn’t have been pretty. They would have been extremely uncomfortable and draining in the moment, but they would have been better for both of us in the long run.

I’m sure Izabel would have been pissed with me. It’s not like we would have had our talk and cleared the air and she would have accepted that our time together was coming to a close but said feck it, sure we’ll make the most of the time we have left.

No, there’s a good chance that she would have decided to end the relationship right then and there, months before I was due to leave, rather than risk getting even deeper into it and setting herself up for a harder fall.

I believe that’s the main reason why I avoided those conversations: I didn’t want her to leave me. I wanted to be the one leaving, when I was ready, on my terms. I realize now how cowardly and selfish I was. The right and courageous thing to do would have been to lay my cards on the table and let her make up her own mind about how to proceed. When to end the relationship was not my decision to make alone, a decision I made by avoiding those conversations. That was her decision as well. I had no right to take that away.

5 Tips for Courageous Conversations

If I could travel back in time and pull scared, 22-year-old me aside, I’d give him the following advice about courageous conversations…

1. Introduce that elephant

If there’s a topic of conversation that you’re avoiding because you’re scared of some awkwardness or pain or tears, know that you can’t run and hide from it. Instead, think of that resistance as a signpost. It points out the very thing you have to talk about.

Like all things that don’t put us in any physical danger or violate the rights of others, you should step towards your fear instead of away from it.

2. Remember it’s a two-way street

It’s important to remember that courageous conversations are a two-way street. You can’t talk about something if the other person isn’t also willing to talk about it. You can’t force people to have courageous conversations. Izabel tried in vain several times to have such a conversation with me, but I kept sidestepping. I wasn’t courageous enough for it. That was my shit, my problem, nothing more she could have done.

If you do find yourself in Izabel’s position, recognize that resistance as a red flag. If the other person isn’t willing to communicate, you either have to accept their silence and live with it respectfully, or you may want to consider taking drastic action. In Izabel’s case, I expect she would have better off in the long run is she had dumped my cowardly ass right then and there.

3. Seek first to understand

Know how to go about having such conversations. There are good and bad ways to broach subjects. Know how you’re going to get into it. If it’s something about a partner or housemate that especially grates on you, don’t open the conversation with loud accusations and finger-pointing. That’s not going to get you very far.

Seek first to understand, then to be understood. A news reporter gave me a good lesson on this a few years back. She often had to get people talking about subjects they didn’t want to talk about. She wouldn’t run up to the congressman and ask him straight up, “How do you feel about your wife leaving you for a pool boy?” Instead, she’d ask something like, “Mr. Congressman, this must be a very difficult time for you, but I was hoping you could help me understand what you’re going through.” Effectively, what she was communicating was this: “Mr. Congressman, I want to know what it’s like to be you, to be in this situation. Let me walk in your shoes for a while, see the world through your eyes. I’d like to understand, to empathize.”

People open up when you introduce an elephant like that. They know you’re not looking to judge or poke fun, but simply to understand.

Tell the other person that you’d like to get their side of the story. Once you have that understanding, share how you’re feeling. You’ll have an easier time making yourself understood once you know where the other person is coming from.

4. Give it time

Courageous conversations are draining, and they’re rarely short. Don’t try to squeeze one in before the game comes on TV. You’re going to need some time and privacy so you and the other person can hash it out.

Take a break if you need one. Don’t expect to get everything resolved in one session. It often takes many conversations to get where you both need to go.

Don’t cling to an outcome of the other person hugging you and everything being resolved. You can’t force your way to that. Sometimes it happens and sometimes it doesn’t. Don’t hold onto an image of you and your partner (romantic or otherwise) being all pally-pally by the time you’re done talking, a happy ending for all involved. Things may actually seem worse if you take the courageous path, at least in the short term. Judge the conversation on whether you spoke the truth and spoke it with the other person’s best interest at heart. That’s courage, even if the other person doesn’t immediately appreciate it or you feel down afterwards.

Remember, you’re aiming for long-term win-win, and your ego will likely have to suffer a few short-term blows to achieve that.

5. Stay caring

Even if some harsh words are spoken, try to keep the other person’s best interest at heart. Even if the other person attacks you or expresses resentment, be courageous. Don’t keep score. Let the petty things go. Absorb the blows and push caring back. Keep your heart open.

Yeah, I know this is very difficult. I’m certainly no master at it. Just because you know something in theory doesn’t make it easy in practice. That’s why we don’t all have chiseled physiques.

Just do the best you can. And next time, resolve to do even better.

To wrap this up, I should tell you that Izabel eventually moved on to another relationship and managed to forgive me my cowardice. We don’t keep in regular contact, but last I heard she was happily engaged to a legend of a man. I suspect he doesn’t shy away from those awkward conversations 🙂

Meanwhile, I’ve learned to be more courageous in my conversations over the years, with romantic partners and others. I still sometimes fail to introduce an elephant or two, but I keep taking small steps beyond my comfort zone and aiming for that long-term win-win. As a result, I find myself collecting less regrets.