He's really the last person who should ever be thought of that way..
Motto on the Sin Past debacle, so let's treat it the way it deserves, and mention it no more.!
As for the whole loser thing then. That really makes me laugh as even overlooking the girls attention..(Though like Invincible said is it really that unbelievable that a good looking, smart, fit guy would have trouble getting female attention?)I would nonetheless say that given Spidey has fought more villains than probably any other hero in the Marvel universe and survived, that would make him something of a 'winner.'
Seriously, I remember an idea that was floating about a few years back, where it was considered that there could be a story where some all powerful character (think it was suggested to be Thanos..)was going to confront spidey with the idea that his Spider-Sense was allowing him to 'cheat' fate. And that death wasn't too happy about that. And thus was seeking some kind of 'Final Destination' type payback by retaliating on his friends. (Would explain Gwen..)I'm not sure I'd like to see this explored in the regular title but I do think it'd make a great What If story. Not to mention that with Spidey's virtually unparralled legion of dangerous super villains, I think he must be very lucky to have not had anything fatal happen to MJ during their time together. Realistically speaking if anyone was going to have the same kind of touch of death as Kyle Raynor's had with girls, it should be Spidey.
So I would say he's been very, very lucky over the years. Whether that is unrealistic or not depends on your point of view I guess..