Imagine the following situation: I've already approached a girl successfully and we are having a conversation about her interests. She says she is a photographer. Would it be too much if I say something like "I used to love taking pictures when I was a kid, but I don't really do this anymore... other people take pictures of me now." (I say it in a playful tone and I'm not lying.)

Kinda sounds like bragging. When ever I am talking about HER interests, I found it very helpful to use the word "You" more than "I." Girls LOVEEE talking about themselves and really don't want to talk about you lol. You can convey your personality in your responses to what she says and let her find out for herself. Be as MYSTERIOUS as possible. Don't give out information that she doesn't ask you. Now, if she ASKS you if you are interested in photography, then might be a good time to use that line. If you are building comfort and rapport and mutual attraction has already been known and established, TURN OFF THE COCKY/FUNNY and show her that you are a normal human being.

I would need to see the context of what was said in order to give you advice on what to throw in there next but to answer your question... Yes, it sounds like you are trying to brag about something.

Thanks. This was a helpful response )