There are a lot of pros and cons around this. The good thing is, you already know them and know you like them. You know their good and bad points (and they know yours) and very little surprises you because they cannot act with you. You know pretty much what you are getting. So you figure it will all be so easy and it can be, but it can also be very tricky.
In my experience the friends who have unexpectedly found this new magnetism with their ‘old’ friend, sleep with each other first and then ask questions later. If you go the other way around and question first you know there is a good chance that it might not happen and you want it to happen because a) there is something there b) you want to get it out of your system and c) you are horny. You also find it interesting to bonk your friend and see what they are really like in the sack. Are they as good as they have led you to believe? Because they have bragged about it on occasion because they never thought they’d be doing it with you. And then the thought hits you while wondering if your friend is as good as he has made himself out to be. Jesus fuck, am I?
Afterwards the whole episode is often put down as a mistake because that wasn’t meant to happen. A line has been crossed because you are friends. Also people don’t know what to say afterwards. It’s not like you can just get up, say ‘thanks for that’ and leave and you might not have to see them again if you don’t want to. This is different. Friends, I think initially anyway, can then have issues about whether that friend is now regarded as their lover or still just their friend. It can become very confusing. Quite often, people seem to be lovers first and then the friendship comes and this seems all very acceptable. Sometimes it makes very good sense to make a friend your lover though, if it works, you can have both immediately. Also you’ve already met their parents and don’t have to go through that whole, ‘meeting the parents’ for the first time scenario.
The big danger is that there isn’t a heap to talk about after sleeping with them for the first time because unlike someone new they know all your stories. The other thing is. It changes things. What are the expectations now? If it was a ‘one off’ can you still pick up others in front of them like you used to? Do you stop telling them about new crushes you have on others? Do you start a relationship? Can you stay friends if it doesn’t work out? Are you gaining a lover and losing a friend? Or are you simply being a slut and have run out of everyone else to sleep with? These are the things that keep me up at night.
I think the friend-dating thing can come after a crush where you think suddenly you like them but really it’s just a little off balanced emotional stab at desperate dating. Oh my God, crushes can be bizarre. I think half the time we make them up just for something to do when we are single. Life gets boring sometimes and there comes a time where you say,
“Gee, I haven’t had a crush on anyone for a while.”
So you look around and find someone and think, ‘that person is kind of cute. I think I’ll have a crush on them.’ Other times I think they take you by complete surprise and there it is. The Crush.
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