I'm a serial dater, It's hard. especially at my age.
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Edit note: I date purely out of boredom, and to have sex. I make it known I'm moving next year, and I don't want anything serious
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There are a lot of things that go on... I will explain them a little.
1) not getting attached (the woman). Hardest part.... keeping the other person from getting too attached. You tell them "hey we aren't together" and they call you regularly like they are your partner/gf. hey find your clingy ass some more friends.
2) keeping honesty and communication - some girls don't like you dating other people. one girl texted me 7 times tonight...I'm not responding, so give it a rest. one text said "oh, sorry you must be out with your other THOTs." not cool. you getting clingy (see number 1)... you know you aren't my girl. you don't REALLY want to know what I'm doing, but if you ask I'm going to tell you. and technically you can't get mad, so I don't want to hear shit
3)keeping personal boundaries.... I don't let people come over my place. because...they can randomly pop up. do you have a place? cool let's go there... tired of just your place? I'll priceline a room. and I'll pay for it.unless I'm with you (I wouldn't be dating would I???) or can trust you won't pop the hell up. I don't want you at my place.
4) expenses .... see 3 and 5 below. Holy ish balls, its expensive to date, I easily spend 1500+ a month on dates and hotel rooms....
5)Dinner .... I like nice resturants, so I eat out A LOT especially with the dating. I get what I want and tell them to do it as well. IDGAF, I honestly like charming new women and getting to know them. the hunt I love. I easily spend 150 - 200 dollars a date easy. throw in a room or something... that's damn 300 a date.
6)Memory -...Remembering who's story went with what's her name , lmao everybody becomes babe after a few drinks because names that sound a like I'll start mixing them up. who did I tell what story to already. pet names and inside jokes... ugh.
*Bonus. I put in my contact info, where I met them, nicknames, and rate the sex.

7)Keep track - How many times have we had sex? 0.... oh we good lets just have fun.... 1....hmmm was it ok? have you been annoying me with constant contact, good thing is no point in being uncomfortable anymore I've seen you naked and made you cum, full on flirting...we are out again so I want to see if its good or better than I remember or want to try something non-vanilla... 2 times... hmmmm you are cool, but I don't see a future so I will bow out gracefully. 3 times(I rarely get here)... I really enjoy your company, BUT do I like you better than the others to stop talking to them (THIS IS WHERE I NORMALLY SAY NO LOL)
that's my personal life in a nutshell when I'm single.