I’m a 22 year old woman and I’m actively getting to know 4 men (not sleeping with anyone). One of them is 24. I don’t tend to show interests in guys who are close to my age, but I give them a chance sometimes.

During the FIRST conversation (text) he asked me is how I’m able to afford my lifestyle with modeling - because his model friends are struggling financially. I told him that I save my money from modeling, and I’m able to travel as often thanks to my family and my agency. He then asked me what my family does for living, which I found pretty odd. We went to private school together (he left earlier) and haven’t interacted since.

For context: He isn’t a model, but an analyst at a real estate firm. Looks wise, he’s very attractive with an athletic build. He likes to post a bunch of shirtless photos online.

The first time we met, he took me out to a restaurant and picked me up too. He brings the topic of my career back to the conversation and kept on asking what’s next after modeling. He said “your dad is working so hard. you can’t make him do this forever”. Evidently, I won’t be a model forever. This is why I’m going to university and keeping an eye out for other industries. I could say that I’m slightly reputable, to the point that I can start a company and sell out in a day or two (I’ve done it before)..but I’m not in a rush and still brainstorming.

The second time we meet, he proceeds to ask the same question again. He told me that modeling isn’t sustainable and that I can’t keep on doing this forever. Even asked me how much a shoot payed me (I remained vague). He took me to a pretty crowded party (again why I don’t like dating guys close to my age). He insisted that I tie my coat around my waist. I was dressed modestly, but my silhouette was noticeable. I didn’t appreciate the entitlement, given the fact that he hasn’t committed to me..I politely refused and told him that it disrupts my outfit.

The only good thing that I see is that he tries to do alternative dates sometimes, such as ice skating, going to the beach etc. He pays for everything and also drives me home which is about an hour away from his.

The questioning actually got to me and made me feel insecure for a while. I can be overly analytical, especially towards myself, which puts me in analysis paralysis. So questions like that trigger me. I don’t appreciate criticism without a suggested solution. I even asked him what I should do instead, and he dodged the answer.

I went as far as telling this to another man I’m speaking to (told him that it’s a girl who told me this). He got quite defensive when he learnt this and asked me “what do they want you to do, waste your youth?”. He’s more advanced financially and socially, and has actually helped me elevate my career so far.

My question is, am I taking this behavior too personal? Or is he just challenging me in a tough love manner? I’ve never had a man be so invested in my income/career.