‘The Bachelor’: Was Colton Underwood Going to Propose To Cassie Randolph In Bermuda?

Former Bachelor Colton Underwood and his season winner and current girlfriend Cassie Randolph took a romantic trip to Bermuda last week. The couple tanned by the pool, swam in caves, befriended some wild beach cats (some more successfully than others), and drank plenty of rum swizzles. And they posted about it all on Instagram. 

Cassie Randolph and Colton Underwood | Matt Winkelmeyer/Getty Images for MTV

Underwood and Randolph’s trip to Bermuda is actually their first as a couple post-Bachelor. 

“Well, tomorrow we’re actually headed to Bermuda. It’s our first vacation since the show’s wrapped. We’re finally going to go sit in the sand and worry about nothing for a week. It’s going to be nice,” they told E! News before they took off. 

The trip had some Bachelor fans thinking the couple would leave their romantic getaway engaged. 

But, as of today, Underwood and Randolph are not engaged–just very happy and riding high off their perfect beachside vacation. 

Was Colton Underwood going to propose to Cassie Randolph in Bermuda?

We don’t know when this vacation was planned, but there is a chance that this trip was originally supposed to be an engagement trip. There were rumors circulating in April that Underwood was planning a secret surprise for Randolph. The surprise was supposedly going to take place around May. Many fans thought Underwood was planning a romantic trip where he would ask Randolph to marry him. When nothing happened in May, fans were hopeful, once again, to see Underwood and Randolph vacationing in Bermuda. 

When The Bachelor first ended, Underwood and Randolph spoke a lot more about getting engaged. When discussing a timeline, they’d say: “sometime within the next year.” Then, all of a sudden, Underwood and Randolph came forward saying their previous engagement timeline was born out of the pressure they felt to move in together and get married. But they weren’t actually ready. 

“I felt like I had to put a timeline on when we were going to get engaged because it was so abnormal, but I think for us, let’s just be normal, let’s enjoy dating each other,” Underwood told ET.  

“I think, initially, coming off of it, honestly, we felt the need to defend it,” Randolph said in the same interview. “Yes, we’re at this stage, and we wanted everyone to believe how much we cared about each other, because we do, so much, and we thought that was how we’d go about it.”

So maybe, a few months ago, Underwood thought of sweeping Randolph off her feet and whisking her away to a beachside romantic getaway to ask her to marry him, but, for now, the couple is back to taking things slowly and progressing at their own pace. 

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Most likely, Underwood and Randolph got offered to stay at the Loren at Pink Beach in exchange for some Instagram posts. They detailed their stay pretty adamantly, and were almost always sure to tag their quarters. 

Whatever the original reason for the couple’s vacation, it looked as though Randolph and Underwood had a fantastic time. What’s more, at least on social media, they seem incredibly happy and incredibly in love.    

Read more: ‘The Bachelor’: Colton Picks Out Cassie’s Outfits