The first thing I hear is him mocking his own view of relationships in high school. I suppose that's fair, especially given that his view was "I just thought that if you had a crush on someone, you tell them that you like them and then you're like boyfriend and girlfriend. No dates; no compatibility checking; you just tell someone you like them and then you're in a relationship."
From here the conversation takes a turn to pre-Facebook social media (Facebook didn't even exist when I was in high school and even I sometimes have trouble imagining there was life before fb!) They are now talking about MSN messenger, of which I am old enough to have fond memories. She is reminiscing about its eventual decline and he pipes up that he basically only used it for video chats.
Her: "Oh yeah, I remember those video chats."
Him: "Oh, you don't know about my video chats, do you?"
He says this like they were some epic legend that most of his friends are already aware of. (Going out on a limb here before he gets to explain, I'm guessing his video chats are actually only legendary in his own mind and that I can guess exactly what was involved in these "chats".) Sure enough he goes on to explain that girls really liked to strip for him. (I would say that any of a variety of non-PC slut-shaming adjectives apply here, but I'm pretty sure legendary is not one of them.)
Him: "I wasn't even popular in high school. But a lot of girls just wanted to do me. I don't know why they liked me so much."
I don't know why either. Strangely I'm feeling no desire to take my clothes off...
Now girl goes on some rant about how people found out your email address/how they got in contact with you/being added by people you didn't know. I dunno exactly. It doesn't really matter what she was saying; the important part is that it spurred Mr. Self-declared chick bait into talking about how "this one girl added me and I didn't even know who she was. But she started video chatting me all the time. Then one day I accepted a chat with her and she just started taking her clothes off. This was like grade 9."
Cue more self-deprecation.
"I don't even know why girls liked me. I was a skinny little Hindu kid. I had nasty little curly pubes on my chin."
Alright humble-bragger, we get it. You were a loser and yet had a magical ability to make girls' clothes fall off. Taking a huge stab in the dark here, but I'm guessing it had less to do with you and more to do with the girls. I know it's been a few years since I was in high school, but I don't think it's changed much; for that matter, I don't think people change that much.
At this point the bus is coming to the last stop. The conversation (or at least my passive participation therein) concludes with the girl asking if his current girlfriend knows about said video chats. He is quick to respond that she doesn't, which seems to please the girl. Too bad I didn't get a picture of him; otherwise I'd say, maybe she knows now...