Grab Your Alibi And Join True Crime Tribe

She Slept With A Guy On Their Second Date After He Admitted That He’s A Criminal And Bragged That People Are Scared Of Him

profile Bre Avery Zacharski | Jul 17, 2026
Jul 17, 2026
young beautiful woman standing outdoors
admirdervisevi - stock.adobe.com - illustrative purposes only, not the actual person

When someone shows you who they are, you have to actually believe them. So if you went out on two dates with someone who revealed to you that they have a criminal history, would you still be interested in pursuing them?

This woman has been speaking to a guy for a couple of weeks now, and they officially went out on two dates. She did end up sleeping with him on their second date, by the way.

He’s been super kind to her, and he’s paid for all of their dates. She also really is starting to crush on him already. The problem is that prior to sleeping with him, she was clued in to his checkered and criminal past.

He revealed that he used to be a drug dealer, he has been arrested for fighting before, and he’s gotten into dangerous fights where there were victims who were seriously injured. Additionally, he got kicked out of school, and his friends went to prison.

“Deep down, those are all things that don’t sit right with me and are honestly big red flags for what I want long-term. I think I just kind of…ignored it? Because he was nice to me, and I wanted to see the good in him,” she explained.

“After we slept together, we talked more, and he started implying that he still kind of identifies with that lifestyle, saying things like he’s a ‘boss,’ people are scared of him, and that I don’t understand that world because I’ve only seen his ‘nice side.’ That made me feel really uneasy.”

“Another thing that’s been bothering me is how I handle boundaries. There was a moment where he tried to initiate something… in the car, and I said no. He didn’t get angry, but he looked a bit disappointed and said, ‘Say less…,’ and then later asked, ‘Are you sure?’ I felt bad for saying no and ended up acting unsure and then going along with it anyway.”

She is upset that she caved to the pressure he put on her. She did go against her own wishes to avoid making this guy feel let down.

She does like how nice this guy is and how he treats her like a princess, but she does realize she’s swept his criminal history under the rug. He is not what she’s really looking for in a man at all.

young beautiful woman standing outdoors
admirdervisevi – stock.adobe.com – illustrative purposes only, not the actual person

She does feel foolish for sleeping with this guy when he revealed things to her that should have caused her to think twice about getting involved with him.

“I think if I hadn’t slept with him, I would already be pulling away. But now I feel guilty, like I owe him something, or it would be wrong to suddenly change my mind. I don’t know what to do,” she concluded.

Look, nice guys don’t pressure you into doing anything, and they certainly don’t brag about their criminal history (which I’m worried is not exactly in this guy’s past; it’s most likely in his present, too).

She doesn’t owe him anything for sleeping with him, and it’s not too late for her to back away, which would be a wise thing to do. Nobody needs to get wrapped up in nefarious activities.

What advice do you have for her?

You can read the original post below.

screenshot
Pictured above is a screenshot of the original post for you to read

Sign up for Chip Chick’s newsletter and get stories like this delivered to your inbox.

image5
By Bre Avery Zacharski

Hi, I'm Bre, Chip Chick's CEO! I have a degree in Textile/Surface Design from The Fashion Institute of Technology, and... More about Bre Avery Zacharski