


With his beautiful long hair, easy smile, and calm demeanor, Alex Propson immediately won over fans on his first season of Below Deck Sailing Yacht. When Bravo was assembling an all-star crew of Bravolebrities to party for two weeks in Colorado on the latest season of Winter House, Propson’s involvement was a no-brainer, especially given his real-life friendship with neighbor/ Family Karma star Brian Benni. Propson explained the experience: “It’s not like Summer House where you’re there all summer. It’s not like Below Deck where you’re all there to do a job. It’s a fast, intense two-week vacation.”
Since Winter House started filming just days after Scandoval broke the internet, the housemates were hesitant to see Tom Schwartz. Propson, however, was determined to give his future roommate a “fresh start.” The two quickly bonded and “ended up having probably the most romantic relationship in the whole series,” according to Propson. That’s high praise coming from Propson since he has already had several romantic entanglements, and we’re not even halfway through the season! Initially, he had his sights set on Summer House: Martha’s Vineyard (and former Playmate of the Year) Jordan Emanuel, but that quickly fizzled after a disastrous drunken kiss attempt in the hot tub. Looking back on that fateful night, Propson said: “If we went through every drunk regret I’ve ever had, we’d be here for a really long time.”
After he bonded with recently single Summer House star Danielle Olivera, the two had a hot and heavy hook up. “She knew what she wanted. I knew what I wanted. It was very simple and it just worked,” said Propson of their night together. However, when feelings and alcohol get involved, the danger is that Olivera could get a little too invested. “You got to make sure that communication is very clear and you’re both on the same page, which I tried tirelessly to do,” said Propson of his intimate encounter with Olivera. We’ll have to wait and see how their new dynamic plays out the rest of the season.
Propson spoke to Decider via Zoom to talk about his relationships with both Emanuel and Olivera, experiencing “menty bs” in the house, and encouraging Schwartz to pursue Below Deck Med alum Katie Flood.
DECIDER: First of all, have you recovered from BravoCon? Do you have a favorite experience from the weekend you can share?
ALEX PROPSON: Not fully. Every time I think I’m getting a handle on things, I seem to be thrown into something else. I loved all things Winter House, but I hadn’t met a lot of the other Below Deck folks from the other spinoffs. Being on the Below Deck panel and hanging out with them and sharing experiences was really cool. It’s rare that we’re all in the same place.
You were introduced to the Winter House crew via the great Brian Benni. How did you first connect with him?
Brian and I have both been in Fort Lauderdale for quite some time. We’ve known each other for a bit, but only started hanging out recently. We actually met at a bar, and then two days later, I was coming home and I realized he was my neighbor. We live in the same building. That really kicked things off. Winter House is our first trip together, so for better or worse, the experience strengthened our friendship, I suppose.
I have to ask… have you met his parents?
I have met his dad, his mom and his uncle. A couple of weeks ago in Fort Lauderdale, I went out for his birthday. They were all there, and they’re delightful people. I hadn’t seen the show. He won’t let me watch the show. I don’t know why. His mom is adorable. They’re all fantastic.

Your roommate was Tom Schwartz. I know yachties are too busy to concern themselves with online gossip, but were you at all nervous about rooming with him?
Not at all. I don’t know much about Vanderpump Rules either. I had heard about what was going on through social media, but all I really knew was third party information. I like to give people the benefit of the doubt. When I met him for the first time, the Midwest-ness in both of us took over and we became friends really fast. Regardless of what I was hearing, I gave him a fresh start, and I’m glad I did. It ended up being probably the most romantic relationship in the whole series.
I know! In this week’s episode, you’re already saying “I love you” to each other.
[Laughs} Yes, there’s a lot of moral support going on. I think he needed it, and then I needed it. This was my first-time ever doing anything like Winter House. It just worked out that every morning we could wake up and turn over and chat. Our pillow talk sessions have become pretty legendary.
Schwartz needed to have a little fun. Were you instrumental in encouraging Schwartz to pursue a little romance with Katie Flood?
I was definitely pro-Katie. For the first half of Winter House, he was very in his head and rightfully so. He had a reunion coming up, and he was nervous about getting back to LA. He had this drama going on and would spiral out sometimes in the evenings. Everyone knew that a healthy distraction would probably be good for him. He was ignoring his connection with Katie for a while, but everybody was trying to urge things along between them because they’re both so sweet. We’ll see how it plays out, but I think he was able to take his mind off of his troubles a bit.
Let’s get into your various entanglements. You immediately were attracted to Jordan. Do you wish you would have waited to shoot your shot until you were sober and dry?
I mean, if we went through every drunk regret I’ve ever had, we’d be here for a really long time. I think everything goes the way it’s supposed to. There was, believe it or not, a little bit of strategy going into that hot tub moment, but then drunkenness just gets in the way. For the first three nights, everyone was just partying hard. I definitely could have paced myself a little bit, but at the end of the day, we’re all there on vacation.
It’s not like Summer House where you’re there all summer. It’s not like Below Deck where you’re all there to do a job. It’s a fast, intense two-week vacation. We came in ready to go basically. So yeah, no regrets. It made for good TV, and we’re good friends still to this day. Things with Jordan didn’t work out, and maybe that’s for the best.

You talk to Jordan about your anxiety and how different you are in party mode during this week’s episode. Was it difficult to open up to someone you’ve known so briefly?
It was really nice. I had a lot of great conversations with Jordan over the course of the trip, but you just didn’t get to see them. That night in particular, we all just needed to chill out, make it a family friendly evening, and have Brian make dinner. That was the day where it was like, “Okay, we can sit down and have a sober conversation, get to know each other a little bit, vent a little bit.” The previous day, she had been crying and had little mental breakdowns—or “menty Bs,” as we like to call them—and I woke up real anxious that day.
Honestly, that conversation could happen with anybody in the house. We were all close enough and felt comfortable enough with each other after a very short period of time that those types of conversations were happening all over the place. I think that speaks to just how special the cast of that show was and how well we really all got along.
There’s something special about Winter House. I know it’s a show where we watch an assortment of our favorite Bravolebrities hook up and party, but it also brings people with shared common experiences together, people who might not have met otherwise and who can bond in this really intense, but really fun environment. It’s an interesting social experiment to watch.
And speaking on that even further, we’re all contained in a small space. It really does feel experimental in some ways. It’s oddly the perfect setting to really get to know each of these people and their characters better. It doesn’t matter if you watch Vanderpump Rules or Below Deck or Summer House or Summer House: Martha’s Vineyard or Family Karma or whatever. We’ve all been brought to the same spot to see what happens. Given all the different personalities, there’s something in there for everybody.
Well, now that we’ve talked about Jordan, we have to talk about Danielle, whom we love. What first drew you to her?
Danielle just has a certain confidence about her. She carries herself very well. There are two sides to her: this very serious mature business woman with boss bitch energy and the drunk Danielle who just wants to dance and throw her hair all over the place. She’s a fiery person, and that’s what drew us together at first. She knew what she wanted. I knew what I wanted. It was very simple, and it just worked. There weren’t any games. It wasn’t anything weird like that. It just worked. The energy was there. It was so great getting to know Danielle over those couple of weeks.
Do you wish you would have known that she was recently single going into the house?
No, it changed absolutely nothing. However, you need to be a little bit more careful about your words and about how you approach it. You got to make sure that communication is very clear and you’re both on the same page, which I tried tirelessly to do throughout the course of the entire process. But yeah, no, I don’t regret that at all.
Your’s and Danielle’s hook up “is the first glimpse into the case study of how casual sex in this environment is impossible,” according to Kyle Cooke. Do you agree or disagree? Can casual sex work on Winter House?
I agree to some extent. It’s difficult in that setting just because of how intense that whole process is. It’s a fast vacation; it’s a small window; it’s a confined space. One day can feel like a week sometimes. It is hard to engage in something like that because it can get so far ahead of you without your even really realizing. It is difficult, but I don’t think it’s impossible. When two people that have the right mindset are in a healthy place and are able to communicate and sort it out, I think it’s very doable. It felt that way for a while. Eventually, feelings get mixed in…
Feelings and alcohol.
Alcohol [laughs]. Alcohol plays a factor in just about every single decision or scene in that show.
From Below Deck Sailing Yacht and Winter Games, audiences have seen you get you flirt, kiss, etc. with a few different women. It’s clear though, especially with your toast in the “Ex-Games” drinking game, that you value your time with them and care for them. Your connections seem to be very genuine. Are you glad that’s being conveyed on the screen?
I try to be nice and I try to respect everyone, regardless of their gender or their background. Specifically, women are amazing [laughs]. They’re the most incredible creatures walking on the planet. It’s not hard to love and respect women. However, when you’re a single guy, especially in modern society, it’s very easy for certain things to get misconstrued and to end up looking a certain way. I’m glad that the genuineness of these interactions and these friendships comes through the camera. I’m glad that everyone left feeling loved and respected. At the end of the day, that was really the goal. I’m glad it comes through that way.
New episodes of Winter House air Tuesdays at 9/8c on Bravo