A guy kept running away from Eugenie Bouchard on an awful first date, the tennis star has revealed as she was grilled about her love life.

After gatecrashing the Canadian's Instagram live chat with sportscaster Allie LaForce last month, American social media entrepreneur and podcaster Bob Menery pledged to donate $US4000 to charity if Bouchard agreed to a virtual date with him during lockdown.

The former Wimbledon finalist couldn't say no to a good cause for charity and Menery recorded their date, which he played on the latest episode on his podcast Zapped.

He wasn't shy about grilling Bouchard on her love life, who admitted she was a little uncomfortable talking about such things because she rarely dives too deeply into them – especially not with someone she was meeting for the first time on video conference system Zoom.

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Menery asked about Bouchard's previous relationships, whether she's ever truly loved a romantic partner and what her plans are for having a family (she wants three-to-five kids). But on a lighter note, he also got the former world No. 5 to spill the beans on the worst date she's ever been on.

"I went on a date with a guy once, we went to the beach and he had food poisoning and he ran to the bathroom to throw up every 20 minutes," Bouchard said.

"It was just a disaster, it was so bad.

"We tried to chill out on the beach and have fun but he would keep disappearing, behind bushes, to the bathroom in the clubhouse, it was bad.

"We were supposed to go to dinner after but I was hoping, I was like, 'I really don't want to go to dinner anymore because this is awful' and he was like, 'Yeah, what if we skip dinner?' I was like, 'That's great, can you just drop me off at home, goodbye'."

Bouchard's best first date ever involved being invited on a boat – something she couldn't help bring up when teasing Menery.

"Beats a Zoom date for a first date," she joked. "Where's my boat, Bob?"

Bouchard said her longest ever relationship with a guy lasted a "few years", but wouldn't answer when pressed on whether she loved him. "I really don't talk about this stuff," she added as she revealed she's been in three relationships, the last of which ended more than a year ago.

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"It's hard to meet people in person because I'm always travelling. Normally I'm in a different city every single week so that makes it super hard," Bouchard said.

"What do you do? If someone knows who you are then I don't want them to look up to me too much, I don't want them to be a fan.

"How do you meet someone who's not like that? It's tough."

At one point, Bouchard gave Menery a six-out-of-10 for his performance on their virtual date, poking fun at him for bombarding her with questions and saying it's "awkward like this where you're interviewing each other".

Menery was upset he didn't rate higher but the passing grade was sufficient for Bouchard, who ended their meeting by agreeing to a second in-person date with her suitor.