Woman Questions If Her Date Is ‘Testing’ Her Because Of The Location He Picked For Their Second Date

Written on Mar 05, 2026

bored woman sitting on date outside with man at table New Africa | Shutterstock
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A woman questioned whether she was acting irrationally after canceling a second date after he revealed where he intended to take her. She had two specific requirements for their dinner date, and he didn't meet either of her requests.

The 28-year-old confessed that she had met a man on a dating app and the first date had gone well, but when it came to planning the second date, she felt the location he had picked wasn't respectful in the slightest. Because of that, she decided to cancel the second date altogether and is now wondering if she was justified in doing so.

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A woman questioned whether her date was 'testing' her by choosing a cocktail lounge for their second date.

In her online post, she explained that when they were planning their second date, he seemed keen to plan their dinner. He'd asked if she had any dietary restrictions, and she told him that she didn't eat red meat and that she didn't drink because she was a recovering alcoholic.

"I have almost two years sober and we discussed at length during our first date what we are both comfortable [with] in terms of substance use. I told him directly that I don’t mind if a date has a drink with dinner, but that I will never again touch alcohol again," she wrote. 

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woman who told her date she was sober questioning his choice of cocktail lounge for second date buritora | Shutterstock

The night before their date, he told her that he made a reservation at a place that she'd never heard of. Deciding to look it up, she discovered that it was a cocktail lounge. When she asked if this was the right place, he confirmed that it was and explained that he liked their small bites menu. 

"I checked the menu and [there] were only a few options — a meat and cheese board, with only two cheeses and four meats, (no substitutions for extra cheese instead of the meat allowed per the menu), a pepperoni pizza, a burger, and a cheese pizza," she continued. "I wasn’t that upset, but was a bit confused that it was a cocktail lounge with only one option that I could enjoy."

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Her date also told her that they could go to a second bar for a 'nightcap.'

Upon hearing the second location, she was officially thrown off. Especially since she had told him that she didn't drink at all. Neither of the locations he had suggested offered dinner, which defeated his whole insistence that they go out to eat.

"I genuinely am okay at restaurants that have alcohol options, but I was honestly a little [shocked] at the suggestion of two bars. Not restaurants with alcohol options. These are, first and foremost, bars," she pointed out.

woman looking up second date locations which did not meet her requirements PeopleImages | Shutterstock

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She decided to take the evening to figure out how she felt, then texted him the next day that she wasn't comfortable going out with him again. Her gut instinct told her that choosing to ignore the only two restrictions she gave him felt like a test to see how much she would be willing to compromise on when it came to a future together.

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A date should respect boundaries, even if they are still just getting to know each other.

Getting to know another person is not an invitation to ignore their boundaries. There was a reason she told him about her dietary restrictions and her sobriety, because they are important to her. He completely ignored her needs in favor of his own. Was it a test? It's hard to say without hearing his motivations, but it was definitely a sign that he was not the type of person who respects boundaries.

Addiction treatment specialist Brandi Ganz explained that when it comes to dating as a sober person, "the decision rests with you to determine the bounds of your own comfort and to exercise those boundaries when it is needed." This woman was open and honest about her sobriety and about what she was comfortable with when it came to dating someone who was a social drinker. Even if his obliviousness when it came to her dietary restrictions could be overlooked, a cocktail lounge and then a nightcap were definitely blatant red flags.

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There is no reason to go on a date with someone if you can tell that they clearly don't respect your boundaries. For this woman, the issue wasn't about her food preferences or the vibes of the places he'd picked; it was about whether he was actually listening to her needs. If this is how he approaches a second date, then it's probably safe to say she made a really good choice cancelling.

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Nia Tipton is a staff writer with a bachelor’s degree in creative writing and journalism who covers news and lifestyle topics that focus on psychology, relationships, and the human experience.

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