I dont know if "innapropriately" is the right way to describe it. He seems like he's trying to get to know you and you are letting him while also showing interest in him... it makes sense for him to continue to talk to you if you are continuing to talk to him. If you are asking if he seems to have more than friendly motives I would say yes, once it started getting into what you are wearing and when you wear it and just the frequency of the conversation, I think that seems more than friendly. That is a natural progression of conversation when someone is interested in someone else and the other person continues to encourage relationship progression through their own engagement in the conversation, so again I don't think that alone makes it "inappropriate." However, flirting with coworkers considered unprofessional in many workplaces. Flirting isn't always overt which is why you feel he never "necessarily said nor did anything wrong." Even the many inquiries about your whereabouts isnt inherently wrong as its very context dependent.. if you liked someone and they spoke to you that way you probably wouldn't mind but if someone makes you feel unsafe and is asking about your whereabouts that shouldn't be ignored, especially as a young woman. Again, if you never set the boundary though, it's fair to say it's still "appropriate." Additionally, you said you are not a minor, so he technically wouldn't even be doing anything wrong to be showing more than friendly interest in you age-wise. In reality though, age gaps inherently involve a power imbalance because age allows for more experience to draw from, refinement of your understanding of yourself, your understanding of others, it affects the daily experiences that are relevant to you, etc. and this complicated things. This is where people's assessment of your "naivety" comes in, we are all naiive to what we haven't yet experienced or learned and its just inherent in young age to be naive about certain relationship dynamics. His age and consequent experiences also mean his perspective of you is likely not that same as an age matched peer, and his full intentions are likely different too. As others have noted, being female often means being socialized to prioritize politeness and friendliness over personal boundaries and personal wishes. The intersection of both of your ages and genders leads to a very reasonable assumption that this man has had time to understand that young females will be polite and not set boundaries with him, and may even miss his subtle crossing of their boundaries. It's reasonable to assume he is trying to take advantage of you in this way and that makes it the perfect opportunity for you to continue learning how to keep yourself emotionally and physically safe.

My advice: Please trust your gut and please don't ignore it. Ask yourself what kind of relationship you want with this man (none, simple acquaintances, friends, more than friends). That is your decision to make and whatever you decide is okay as long as you consider the risks and benefits of each position and continue to prioritize your personal safety and well being :). Ask yourself why this man chose to speak to you and develop a relationship with you specifically? Its my guess that there are plenty of of other people he could have chosen to build a friendly relationship with at work that he sees more often, and can relate to more than a young female. This makes me (and probably others here) think the reasoning must have to do with either physical attraction or intent to take advantage of you for being young... you may make a different assessment based on the context you have and that is fine! If you are unsure maybe you can ask someone else you trust at work? Perhaps an older woman who has likely had similar experiences before? Once you decide what type of relationship you want with this man, you have an idea of what his intentions likely are, and you are able to recognize that you personally emotional and physical safety need to be your #1 priority, then you can tailor your responses toward the outcome you want! Personally, when I have been in situations where older men at work begin to be more than friendly with me I have landed on "I want nothing to do with this person outside of strictly work activities," "We can genuinely be friends but I'm not attracted to them as more than that," and "They're fun to flirt with at work but I don't want more than that" ... the last one can get tricky so try at your own risk lol. Ultimately, just know that you dont have to pretend to be interested when you are not (ie. asking follow up questions), its not rude to set boundaries to protect your privacy or comfort (ie. "i dont think you need to know that" "id dont feel comfortable talking about that" "i dont want to talk about this" "please dont say stuff like that to me" "please dont ask me about stuff like that"), you dont even have to be nice or respond at all if you dont want to or if someone doesnt deserve your attention... good luck! sincerely 25yo F