Your feelings are absolutely valid, and it’s not an overreaction to feel upset by comments that seem to diminish your experiences or insinuate distrust. Here's a deeper breakdown of what's going on:

Why His Comments Are Hurtful

1. Implying a Lack of Agency: When your boyfriend assumes that any attention you receive is solely because of your gender, it can feel like he’s ignoring your accomplishments, personality, and the full context of your interactions. For instance, the comment about the compliment on your presentation dismisses the hard work you put into it and reduces the entire experience to just "a guy" noticing you because you're a woman. This can make you feel like your value in those situations is being minimized or overlooked, which is understandably frustrating.
2. Trust and Autonomy: By constantly bringing up whether the person interacting with you is a man, it suggests that he might not trust you to handle or navigate these situations on your own. It could also feel like he’s questioning your judgment and your intentions, which can be demeaning. When you’ve already told him that these comments hurt, it’s natural to expect that he would respect your feelings and stop making those assumptions.
3. Undermining Self-Esteem: Your self-esteem boost from feeling good about yourself (like when you did your makeup) should be celebrated, but his comment about impressing a guy undermines it. It makes your positive feelings about yourself seem like they’re only valid if they’re tied to someone else’s potential approval, which is dismissive of your own autonomy and self-worth.

You're Not Overreacting

It sounds like you've communicated how these comments affect you in the past, and he continues to disregard your feelings. That’s more about a pattern of behavior than one isolated incident. It's understandable to feel upset when someone repeatedly dismisses your feelings, especially when you've already been clear about how those comments make you feel.

It’s not overreacting to want your partner to trust you and see you as an autonomous individual, rather than someone whose worth is measured by the attention she gets from men. In a healthy relationship, both partners should feel trusted, valued, and respected.

How to Approach the Conversation

You’re already aware that you need to communicate how these comments hurt you, but it’s important to approach it in a way that promotes understanding. Here are a few tips for framing the conversation:

1. Choose the Right Moment: Try to find a time when both of you are calm and can have an open, honest conversation without distractions. Avoid doing it in the heat of the moment when emotions are heightened, like after an argument.
2. Use “I” Statements: This helps avoid sounding accusatory, which could make him defensive. For example, you could say, “I feel hurt and frustrated when you assume that attention I receive is because I’m a woman or when you ask if it’s a guy. It makes me feel like you don’t trust me or my ability to handle these situations.”
3. Explain the Impact: Share how these comments make you feel personally. For example, “When you say things like that, it makes me feel like you don’t value my accomplishments or the work I put in. I want to be recognized for my efforts, not just my gender.”
4. Set Boundaries: Let him know what kind of comments or behaviors are not acceptable. Be clear about what you need moving forward. For example, “I would appreciate it if you didn’t make assumptions about who interacts with me or why. I want to feel trusted and supported in the relationship.”
5. Encourage Empathy: Encourage him to understand things from your perspective. You could ask, “How would you feel if I constantly questioned your interactions with women, assuming that any attention you received was because of your gender? Wouldn’t that feel disrespectful?”
6. Reinforce Your Feelings: You’ve already expressed how these comments make you feel, so reinforcing that these conversations are important to you is key. Let him know that you want a relationship built on mutual trust and respect for each other’s autonomy and individual experiences.

Conclusion

It’s not overreacting to feel upset by these comments, and your feelings are valid. It’s important to communicate how these actions make you feel, especially if you’ve already expressed your discomfort and nothing has changed. In any relationship, both partners should feel heard, respected, and trusted. Your feelings are important, and setting boundaries around how you’re treated is essential for maintaining a healthy dynamic. If your boyfriend values the relationship and cares about your feelings, he’ll be willing to make adjustments and show more respect for your experiences.