I'm going through my past and just gathering all the mistakes I've made with women and all the great things I did in order to improve myself overall.

Anyhow, I recall this one instance where a friend/co-worker asked me to ask another co-worker if she had a boyfriend. I didn't have a problem with that. I simply asked her if she had a "prince charming" in her life. She enthusiastically said no and ever since then she thought I was interested in her and became flirty with me (really cute with a very nice ass).

Anyhow, the lesson here is, "Never have a friend do the asking for you." You don't really want to risk someone thinking that you're a coward.