Search Results: talking about the opposite sex

So my boyfriend and I have been having trouble with the limits of talking to the opposite sex in our relationship. We have been dating for about 8 months so we're still learning about each other and such.

This weekend we were away together with friends too and a guy I used to hook up with a year or so ago snap chatted me (i'm not sure everyone knows about snap chat but it's basically you send someone a picture and you can write on them but you can only see them for a couple seconds then they delete automatically). He was with a bunch of people I knew from high school and he was sending me videos of all them hanging out since we all went to high school together. I didn't think I needed to tell my boyfriend at the time because I didn't think anything of it and I hadn't talked to the guy since my boyfriend and I started dating.

Then the next night, a girl my boyfriend works with drunk texted him and I had never heard of this girl before but I could tell that she had a crush on him from what she was saying. And I was jealous of course but I just told him to remind her that he has a girlfriend and he was with me at the time so that she would stop texting him.

The next day, my boyfriend was looking through my snap chat and saw the snap chats from that guy I used to go to high school with and hook up with and he naturally got angry and said I should have told him about it sooner, but I didn't really know I needed to and I couldn't show him the snap chats because obviously they delete automatically.

Basically, I know it makes him uncomfortable for me to text other guys especially ones I've hooked up with and I don't normally talk to the guys I've hooked up with at all but I had a lot of guy friends in college because I had guy roommates and such so I don't want to have to stop talking to all my guy friends all together. And my first boyfriend of college still calls me occasionally and stays in touch even though we haven't dated in 6 years or hooked up in years because we're friends, but I can tell it still makes me boyfriend uncomfortable but I don't know what to do.

And I understand he needs to communicate with people he works with, but if a girl who has a crush on him is drunk texting him, even if he works with her, is that crossing the line?

What do you guys think? And this can relate to same-sex relationships as well.

For those WHO USE SMILEYS (there's plenty that don't):

How do you meet your smiley quota? Do you reserve them for times when you're flirting, or do you just use them to get your point/tone/feelings/emotions across?

Put another way, how often do you use smileys when talking to someone you're NOT interested in?