A friendship, a five-hour coffee date, and a surprise proposal in Montenegro

Ishita Kumar and Shivraj Singh first met at a birthday lunch in 2023 through mutual friends. Although they both worked for IndiGo, their first meeting happened completely outside work. Singh had apparently already heard about a “new attractive girl at IndiGo” and was curious to meet her. Kumar’s first impression was much less dramatic. She thought he was cute, but surprisingly quiet. Neither of them left that lunch thinking they had just met their future fiance.

A few months later, they bumped into each other again at an office party. This time, they followed each other on Instagram, and the occasional DM quickly became two years of relentless banter. Singh discovered Kumar’s private Instagram account, where she posted her most unfiltered and goofy self, and decided she was someone he needed to roast every day. Kumar responded by giving him the nickname “Raju”, which he has apparently disliked from the start.

By late 2024, something between them had begun to shift. Conversations that once ended naturally kept going, and by December and January, they were talking constantly. Flirting slowly entered the friendship, although neither of them really acknowledged it. They had not been looking for a relationship, which perhaps made it easier. There was no trying to impress each other because they already knew the most ridiculous versions of themselves.

They eventually started dating on March 11, 2025, although there was no official asking out. After months of talking, Kumar finally suggested they get coffee. Singh drove an hour to pick her up, and they headed to Boojee Café in Bandra. What was supposed to be coffee turned into five or six hours of conversation. At some point, Kumar asked the obvious question: was this a friendship, a relationship, or a situationship? Singh admitted he liked her but could not tell if she felt the same. Kumar confessed that she did too.

There was still no grand romantic moment. They barely managed a goodbye hug. Later that evening, Kumar asked Singh if he could call her. He FaceTimed instead. That first phone call became a habit, and March 11 became their anniversary.

By the time they travelled to Montenegro a few months later, marriage was already part of their conversations. Kumar had even given Singh a list of things she absolutely did not want in a proposal: no giant signs, no hidden crowd, and no audience. She wanted the moment to belong to the two of them, with a photographer quietly capturing it.

Singh planned the proposal at Horizont, overlooking the Bay of Kotor. The only problem was that Kumar nearly discovered the entire plan the night before. Unaware of what was coming, she took Singh to the same spot and casually told him it would be the perfect place to propose. He somehow kept a straight face.

The following evening, Singh insisted they dress up, take their convertible, and drive up Montenegro’s Serpentine Road around sunset. His suspiciously sweaty hand and unusually quiet drive were already giving him away. At Horizont, Kumar spotted candles, a setup, and a photographer. Singh began his speech, became emotional, and finally told her, “Today is National Girlfriend Day, but I was thinking, why not retire you from that title forever?”

He got down on one knee and presented her with her dream ring.

Their families had already embraced the relationship, with both sets of parents meeting just months into their relationship and quickly giving them their blessing to decide when they wanted to marry. Now, the couple is preparing for their December 2026 Anand Karaj at a Gurudwara in Mumbai.

For Kumar and Singh, the engagement marks the next chapter of a relationship that began without a plan. Two years of friendship became a relationship almost without either of them noticing, and a casual coffee date eventually led them to Montenegro, a dream ring and a promise of forever.

Lead image: Montenegro Proposal Photographer

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