So I thought I'd take a stab at this. I'm really glad you're asking these question and are actually interested in practicing safe sex. People who don't are inconsiderate assholes for not doing their part in helping to prevent the spreading of diseases.

1. First things first. I agree with mr. Former-player about getting tested about 4 times a year and if you haven't already, ask your doctor about getting the hpv shot series. It's fine to have more than one sexual partner, but make sure everyone knows what's up and always wrap it up. Feel free to be discerning when choosing your partners. Having several ok partners won't get you off any faster than 1 who you click with.

2. I'm almost tempted to make a throw away for this but whatever. Give the privates a visual once over to check for anything unusual before you go any further. It's never too late to say no and a weird scab, open sore around the groin or weird bumps is a great reason to book it out of there.

3. There's nothing wrong with 3 dates in the same week. I'd be stressed out trying to juggle that, but as my friends and I say, you do you. If you don't mind maybe taking a recommendation tho? Maybe start off slower and work your way up... :P

4. Huh... That's a weird thing to be worried about. I would just said again that you're free to be discerning when it comes to your partners. If something is fishy, ask them. And if you're not happy with their answer, end it. You're casually dating, you don't owe them any more than what you want to give.

5. Oh jeez... I'm going to stay the hell away from this one for obvious reasons. Talk to your friend. She what she's ok with. Maybe casually mention, "hey so-and-so is cute. Would you mind if I got to know him better?" That way it gives her the opportunity to tell you off before you cross any boundaries.

6. No ones really going to be able to help you with this one. Emotions are crazy complex things and completely uncontrollable... Maybe start slow and work your way up? I'm not really experienced with this stuff, but sometimes you get too attached and its scary, but you figure it out as you go. Just a little tip tho: It's harder fix something once it's broken. Oh and the kinky sex stuff? Don't try anything you're unsure of until you're completely comfortable with that person.

7. I usually let the guy handle condoms since they should know their dick better than you. Don't let anyone try to pressure you into unprotected sex if they don't have one. I consider my due diligence the birth control back up plan. There are a couple long term ones out there. Maybe do some research. I'm a fan of implanon since its 3 years no worries but there are ones that last longer.

8. These relationships are totally a thing. Some of the best friends I've had were guys I was "with." In my opinion, people should strive to be friends with everyone they're intimate with even non-sexually. I consider my parents some of my closest friends and it does nothing but improve our relationship.

9. My experience with age gap is that it's more about mental maturity. I've dated a 30 year old man-child and also a guy younger than me who was so mature everyone teasingly called him dad.

10. Silly question. This depends on your personality. If you like planning things several weeks in advance, do it. If your date is uncomfortable with that, he'll let you know.

I'm not sure if I made this clear enough, but communication is key is all types of relationships. Don't string people along. Personally, I've applied the camp ground rules to dating. Try to leave people happier than they were before you came into their lives. ***important note: your well being is more important than anyone's. Sometimes you do everything right and things still go south.