Captain Glenn Shephard Says He Once "Came Close" to Hooking Up with a Charter Guest

There's always a lot of romance on the high seas, as we've seen on Below Deck over the years. And though that's not something the captains typically get involved in, that doesn't mean it hasn't happened for them in the past.

Captain Glenn Shephard answered fan questions directly via text message on Tuesday, March 15, and during the Q&A, the Below Deck Sailing Yacht boss was asked if he ever dated a fellow crew member or charter guest. "I came close once to hooking up with a guest, but I couldn't because we were both older, and it's not quite the same thing, but then it sets a really bad example and it gives the crew carte blanche," Captain Glenn said. "So we kept it platonic, and we still keep in touch, but nothing ever happened."

He then recalled a moment during Season 1 of Below Deck Sailing Yacht when he briefly socialized with a guest during their charter. "In season 1, I had a good rapport with one of the guests, and she invited me for a drink on the flybridge. We went up and had a drink and a nice chat, just the two of us," Captain Glenn shared. "She was a very nice person, but, you know, I was just being polite and we just had a nice conversation, but I wasn't going to let it get any further than that. Again, for the same reason, because that kind of thing is discouraged — and that was during charter. The crew are not meant to fraternize with the guests in certain situations. That's a really big no-no."

Captain Glenn said that he's never met up with a guest after their charter has ended. And even when guests ask crew members to join them off the yacht at places like clubs while the charter is in progress, the yachties are still supposed to keep things strictly professional. "Even then you would expect the crew to be discreet and not accept any advancements because that's not really meant to happen," he said.

However, Captain Glenn has dated a yachtie before. "I was dating a chief stew, not on the Parsifal, but on another boat for a while," he revealed.

As for Captain Glenn's current relationship status, he confirmed that he is not married and doesn't have any kids. But, he shared that "there is this one lady that I have my eye on," although he said that "she doesn't want to be out there in the public."

Captain Glenn shared a similar tease about his current love life when Bravo Insider caught up with him prior to the Below Deck Sailing Yacht Season 3 premiere. "Well, there is a particular woman that I'm kind of chasing," he said. "But she prefers to stay out of the limelight, so I don't really talk about it online. So that's the situation now."

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