I’m in a situation I’m a little apprehensive about. I like this guy, a coworker and he likes me too. However, due to religious differences, I can’t date him. It’s not like I’m intentionally playing hard to get yet he seems to keep chasing me. I’ve turned him down and explained to him the situation two times. I’m not sure how to vet his intentions and who he is as a person. This is all online by the way.

The first time after he asked me to be his date for an event I turned him down and told him I wouldn’t be able to date him or anyone from a different religious background. He acted cool about it and we continued talking about whatever in-depth conversations we were having. So I was like ok, glad he’s not mad. We continued texting and he continued to show signs that he likes me but most of the time I either just smile or kind of dismiss it by teasing him about it, which I know makes it turn into a playing-hard-to-get game. I didn’t want to lead him on and make either of us hurt. We did stop talking for awhile when he went on the trip for the event but started talking again and he suggested plans for us although I think it was just playful talk.

The second time, I told him how I felt about him and that unfortunately with just how things are on my end, I can’t go along with how I feel about him. He told me what he liked about me but wasn’t sure either if we can move things forward but was still open to us meeting. I figured it was fine to share since I won’t be talking to him much anymore. We didn’t talk for almost a week and I had gotten the closure I needed by sharing how I felt. 4 days later he texted me showing me something that reminded him of me and that it would be beneficial for my love life. I was getting that he just wanted an excuse to talk to me because what he shared with me isn’t something that would show up in his feed (not going to be specific here so I don’t give away too much personal info). We had a small conversation and I told him about an event I would be attending and he volunteered to be my date if I wanted one. I said sure because I was nervous about going alone. The event won’t be happening for a while. I was surprised he reached out to me and then offered to be my date but that’s probably because I confessed how I felt and now he knows there’s a chance at whatever he’s thinking.

I have a lot of questions:

  1. Is this considered him chasing me and a red flag to look for because I’ve turned him down a few times and only abusers or guys with issues would continue to chase a girl? From his social profiles, he likes winning and knows he is a very capable, successful guy in his career.

  2. Is he just after sex? Our conversations are clean. He never makes it sexual with me. He said he doesn’t agree with casual sex because we both know women will get attached. Though I know this doesn’t mean he won’t do it. I don’t know his relationship and sexual history. He is not a charmer or smooth talker and prefers to get to know me and my beliefs on various topics. He seems mature and he is very logical so it doesn’t seem like he would act irrationally towards me. He does know my views on sex before marriage and I’m unsure if this would be viewed as another conquest for him to win.

  3. I’ve had times after I talked to him and realized that I may have emasculated him too much with playful, mean jokes that question how good he is as a person or at something. Today I was starting to feel maybe what I had been doing so far is slightly emotionally abusive because I’m coming across as hard to get and dismissing his interest in me while keeping him in the loop. I don’t intentionally do it but end up doing it because if I’m receptive to him, it will lead him on. I don’t want this to backfire on me where if he gets what he wants, he tosses me aside or if he doesn’t get what he wants, it gets unhealthy between us. I figured if I were to continue talking to him even as just a friend, I could just be nice, show appreciation or acknowledgment, and show some emotions instead of being “mean.” But I’ve always had a problem being receptive with men and the only way I know how to flirt with them is to kind of diss them or challenge them. When is it too far with challenging or teasing a guy about who he is?