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Here Are The Most Awkward But Constructive Conversations People Have Ever Had

Nobody likes an awkward conversation, but they can actually do a lot of good — especially when it comes to checking in with your friends about their mental health.

1. The Girl on the Train

"One day I got on the train and saw a woman quietly crying, so I sat down next to her and told her that, whatever it was, it was going to be okay. She thanked me in a heavy accent and proceeded to explain what was wrong. Though it was hard for me to understand, I put together that she was upset over an altercation with her son. I kept smiling and nodding and hoping she understood what I was saying in return. Eventually, she stopped crying and thanked me for talking to her."

—Mandy C.

2. TFW College Stinks

"At a party in college, some friends and I secluded ourselves in a corner of the hallway and were talking and laughing there. All of a sudden, my crush sauntered over to us to say hi — and just as he did, I accidentally let out a very, very terrible, but silent, fart. We all chatted for a minute, and then my crush looked around and said, 'Wow, it smells REALLY bad right here.'

"I burst out laughing and had to run away. But in the end, he and I dated for over a year, and it was good that I knew he liked me even despite my terrible farts!"

—Denise Y.

3. Reality Bites

"When I first moved to NYC, I casually mentioned to my new roommate that I had always hated reality TV, to which he responded that he was a longtime, diehard fan of the genre. He had actually worked as a stagehand on the set of a few! After a few awkward apologies, I agreed to watch a couple different shows with him and let him give me some insight. At the end of the day, I actually totally understood the appeal, and now I love New York!!!"

—Will S.

4. An Essential First

"I remember my short-lived relationship with the first guy I ever dated, who was so incredibly sweet and giving. It was my first-ever gay relationship, and I was still uncertain of what I was looking for within this uncharted territory. Though this boy was a great person, I just didn’t feel the spark I was looking for. Eventually, after a month of anxiety, I broke things off and just spelled everything out for this guy. He was so patient and understanding, and I really appreciated that. We’re still friends today."

—Neel Y.

5. The Story of Man and Woman

"When I was in college I was dating a girl, and, although she was amazing, things weren't going well between us. So we had the breakup talk, and it was predictably excruciating. Unfortunately, circumstances later that day worked out so that I then had to get in a car with her for a 3.5-hour drive to the hometown we shared. This was, mind you, less than 3 hours after our tumultuous breakup."

—Eric S.

6. ...And, Um, Another Story of Man and Woman

"When I worked in retail, I once helped a woman and a man accompanying her who was very gracious and doting. When she was in the fitting room and he was waiting, I asked if she was his mother, as she looked quite older. He said, 'That's my wife.' I hid in the stock room for the next 20 minutes but still asked the cashier if I had gotten the commission."

—Emily C.

7. Best Friends Wherever

"When I was a sophomore in college, I started to think about studying abroad. I privately did some research, but I was REALLY nervous to tell my roommate. We'd been paired together as strangers our freshman year, hit it off, and agreed we could live together forever, and I was nervous she would be upset with me for 'abandoning' her for a semester.

"For a few weeks, I fretted over when and how to tell her, until finally I came out with it. To my delight, she was hoping to do the same! We instantly opened up to each other about our hopes for a semester abroad, helped each other through the application processes, and supported each other that fall when we both began our junior years abroad. We even visited each other in the UK and leaned on one another other when we returned and felt homesick for our respective adventures."

—Casey C.

8. Best Friends Forever (Really!)

"I’ve known one of my closest friends for a super long time — like, this is a since-we-were-in-kindergarten kind of thing. So we’ve always acted super comfortably around one another, and I haven’t always thought of how my words and actions affect her, since we’re usually honest and open and know one another so dang well. Anyway, one day this friend asked to talk and told me that the way I casually joked about her relationship with her boyfriend was hurting her. I never for a second thought anything I was saying could be perceived as harmful, but I was forced to take a step back and look at our friendship from her perspective. It was eye-opening, genuinely."

—Stephen J.

9. Morals for Spring

"One year during spring break, my boyfriend and I decided to go abroad. It was our first time traveling together, so, while it was exciting, it also came with a lot of firsts and us seeing sides of one another we hadn’t really been exposed to before. My boyfriend, for example, proved rather irritable and anxious for a great portion of our time there. Our relationship had seemed so perfect before this trip, so I was nervous to create any sort of rift. When I finally (and nervously) sat him down on our second-to-last day in France, he actually...totally got it and admitted that he knew he’d been acting in an improper manner. And though we broke up months later, it was for totally different reasons!"

—Vanessa U.

10. It's Someone Else's Party and He'll Cry if He Wants To

"One night about a year ago, I was at a going-away party with a close friend who I loved dearly but had been feeling some resentment toward over a number of unspoken issues. After a couple hours together, suddenly everything I'd been passively keeping to myself for months just spilled out. It wasn't the most appropriate setting, but my untimely confrontation ended up repairing our relationship in a really essential way."

—Kyle D.

11. Lovers to Friends

"When I was in high school, I was dating a girl who I considered my best friend as well. We went to prom together and spent all of senior year side by side. This made things much more difficult when I eventually came out to her as gay. At first, she was angry that I’d broken up with her, and I think she felt lied to and hurt. Eventually, though, we talked through things, and I explained to her that this was not the same thing as a typical breakup and just sort of detailed all the nuances and intricacies associated with coming out. We worked through our issues over a couple of months and became closer than we’d ever been before."

—Gregory B.

12. A Misunderstanding Gone Right

"I'd noticed recently that my mom had been making remarks about the medication I’ve been taking, which I perceived as criticism. I had held my tongue pretty well for some time, but, one night recently, our conversation took an awkward turn...for the better. It was a tough conversation, but it was the most open and honest I had been with my family about my depression.

"I had always seen them as critical and judgmental of my decision to get help, but I realized what I thought were negative responses were actually their attempts to better understand me. Speaking openly with them about it lifted a major weight off my shoulders and felt like a milestone in our relationship."

—Clark M.

Images from iStock

Leverage life's awkward moments and learn how to start a conversation about mental health with a friend at Seize the Awkward.