By Josh Sutton

The hard hitting realities about dating you’ve probably already told yourself, but were too stupid to listen to.

Female, 23, dating

If you’re “seeing someone” and going on dates, when does it turn from “just a thing” into an actual relationship? Does it require “the talk” and how do you bring that up?

To quote the 2010 Owen Wilson hit How Do You Know, “For me its when I start using condoms with the other women”. Now, depending on your reaction to that, you are one of two people. If your primary response was a chuckle, stay free my friend and take in all that the dating pool has to offer. However, judging from the question being asked, you were likely appalled at such a comment. 

Relationships, casual or serious, are all about expectations and boundaries. With open communication between parties, ‘the talk’ never really needs to be brought up. Instead, it is something you naturally grow towards. You are introduced into areas of an individuals’ life they hold close to them. You learn more about them as a person, you meet their family and friends, and hell they may even just start referring to you as the gf/bf.

Now, my hunch through experience would have me believe that you are into this individual and have eyes for only them. That’s great- buy a bottle of Jack because if you are really questioning where you stand in a situation, it’s likely next to another two or three individuals your someone is seeing.

 I have always been a firm believer of upfront honesty even throughout my more liberal college years. If a clear path of what both parties were looking for wasn’t defined, call it out. Be bold. Ask. Make that move- but have that whiskey standing by. You will come to discover that this is the end of the road or that both of you are feeling the same way and have been feeling uneasy not knowing how to define your relationship. Either way you have gained clarity and confidence. The confidence to move forward into a great partnership, or the confidence to call out some schmuck who didn’t know what he or she wanted, but was simply taking advantage of your precious time.

Female 22, dating

What if you like someone who is in a relationship and you don’t have any intentions on being a “home-wrecker”, but you feel that they like you too? Should you say something? How should you go about it?

This one is tricky. You could be mistaking kindness for flirting. You really need to judge their current relationship, as well as the one you two have established. If this is a newer friend and they constantly bitch about their current partner while making suggestive comments your way, chances are it’s game on- but be leery.

If you make a move and it doesn’t get rejected then you are potentially setting yourself up to get involved with a cheater (and be a home wrecker yourself). Ask yourself if this person is really someone you see yourself with long term. If so, tell them. Maybe they feel the same, maybe not- but you have nothing to lose. A new friend, fuck that. Nothing is more heart wrenching and humiliating than being the sad lonely shadow.

You either spark some magic or cut the person out of your life, and let them know exactly why. You can’t just be friends with someone you have feelings for (same applies to your ex, stop drunk texting). You need time apart to collect your emotions and mentally move on. Only then is just friends an option, yes this applies to your ex as well.

Female, 22, dating

What do guys actually think if you sleep with them right away? 

“Yes, I got laid” That’s it. No thought directly related to you at all. If we have asked you on a date we have pictured you naked, what sex with naked you is like, if naked you does (insert own random fetish). Personally I have never thought less of any woman who I have slept with on a first date or without a date for that matter. Sometimes the chemistry is there and why not have a passionate love affair for a few weeks before realizing you really don’t have that much in common.

Now if you’re asking yourself this question the morning after every other first date then he probably thinks you are a whore. Lucky for you he thought this before (nothing changed after the sex), because nowadays nobody can’t keep their fucking mouth shut, and it’s likely this reputation that got you asked out in the first place.

 If it’s a rare occasion, hang on for the ride. One passionate love affair is worth all of the heartache I have ever experienced combined. If it’s the latter, consider holding out a bit if you are really looking for something more. With that kind of a rep, it’s likely you have a few bedside talents that are locker worthy chatter other than just being willing.