If I was with someone who was insecure about their penis, I wouldn't blame them for "whining," but I would do my best to convince them that they're fine the way they are. If they continued obsessing over it, THEN it would get frustrating.
YES, it's best to stay confident, and even better, have a sense of humor about it. You know how it's kind of a turn-off when girls talk about everything they dislike about their bodies and take it all so seriously? I feel the same way about guys doing that. It's just a body, every one has quirks.
Wow it requires a special kind of bitchy to actually have the heart to say that to a man.
Also,it's probably best to laugh it off.If it comes down to getting intimate to another partner and you'd want her to know, just make it subtle that you're self conscious about it, if you are, and she'll probably get it.
Girls feel needed and appreciated when they help a guy boost his confidence about any matter, but don't make it her daily job or fish for compliments, 'cause she wouldn't like that.
No, I don't hate guys who whine about having a small penis. I actually feel really sorry for them that they've deluded themselves into thinking all girls require an 8 inch d***. 99% of us are not that shallow and superficial. I can only speak for myself, but I don't give one iota about penis size. Even though I'm a virgin (people always throw that in my face like I have no authority to speak on the matter), I can wholeheartedly say that I fall for the guy, not his d***.
Yeah, your best strategy is to just play through it, ignore it, laugh it off, do whatever you need to do to not focus on it. Most of the time you have more than enough tools at your disposal to give her an unforgetable experience between the sheets.