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Need a completely outside opinion on 3some

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My ex casually mentioned having a 3some with me and current grill. Got your attention?

Background: about 7 years ago started dating qt3.14, lets go with Lisa. We were both at uni, good fun, no ragrats. We dated for about 2.5 yrs, but were totally toxic for each other. Both our grades went down, smoked more weed, always broke, etc. After graduating i got a big boy job (still have it actually) and she proceeded to do nothing. i couldn't/wouldn't support her entirely, plus some other bs and we broke up. Enter grill 2.

I moved a ways away, but still easy to reach and come back to visit other friends. Me and Lisa would see each other in passing, always cool and after while could actually chill like normal friends. During this time i start seeing a grill, lets say Jenny. We've been on and off for about the past 4 years, really only being off because distance is hard to maintain a relationship and i move too much.

So Lisa and I ended up (without realizing it till after the moves) living a few blocks away from each other, and Jenny is over 1500 miles away. We chill, smoke, go to the bars, ya know, normal friend shit. Jenny is coming out to visit in the next few months work depending.

Lisa and i were at the bar the other night and she very casually mentioned that she couldn't wait for Jenny to get here so we could have a 3some. Jenny and i have never been monogamous (see 1500 miles) so not really worried about that. The thing is, Lisa and I have not hooked up since we finished our relationship, it's never even been mentioned, we basically both just ignore the fact that sex is a thing.

I'm so lost /adv/. Do i try to smash with Lisa beforehand cuz 1500 miles is a long way? Do i not risk the friendship? Do i just wait till Jenny gets here and hope for the best? Do i go the Poly route and try to catch em all? I need any and all opinions since literally all of my friends are close with one or both of the two, cant get a non-biased view.
>>
>>17498787

>Jenny and i have never been monogamous
Jenny knows this?
>were totally toxic for each other
You already fuck lisa is not like that would never happend or that the friendship is at risk.
If I were you I would be more worried about if Jenny wants to share you with other woman while she is in town, I mean is not the same, you may need to hook up when Jenny is not there for you but when she is there she probably wants to be only with you (I suppose idk your relationship). even if you are not monogamous thats doesnt implies that she is open to a 3some.

I will try this >Poly route and try to catch em all
They are both friends of you and also friends of your friends so beware
Tell lisa sooner as you can if she wants to try that
>>
>>17499035
>Jenny knows this?
Yes it's not been a secret, i know of some guys she's been with and she knows some of mine

Thanks for the advice yo, hadn't even considered that she wouldn't want to share me when she was in town for a limited time. Glad to have an outside view on what i can't see right in front of my face :)
>>
Good luck, at the final of the message I wrote Lisa but I mean Jenny
>Tell Jenny sooner as you can if she wants to try that
If the two of them are fun girls they probably want to try it
>>
Talk about this and decide this with Jenny first. Lisa is not your gf. If you pop this on Jenny without even discussing it beforehand, that's a big problem.

And as someone who has had a threesome here, if two of the parties are not attracted to each other, it's just gonna be one person having sex with two people at the same time. It can work in the short term but can really cause problems in the long term.

Also, make sure that if you start this, that everyone honestly believes that they'll be cool if things go south (and isn't just saying it to make it work). You don't want to start something like this if it's likely that someone is gonna blow up about it later.
>>
>>17499086
>Wrote Lisa but meant Jenny
I kinda thought so, i got you.

>>17499089
>Talk about this and decide this with Jenny first. Lisa is not your gf. If you pop this on Jenny without even discussing it beforehand, that's a big problem.
Good point, i would much rather see nothing happen at all than fuck things up with Jenny.

>And as someone who has had a threesome here, if two of the parties are not attracted to each other, it's just gonna be one person having sex with two people at the same time.
Yeah I've been there before too, and it ended quickly and angrily. I know there is attraction one way, but will need to see if Jenny is attracted at all to Lisa

Thanks a lot for the advice so far guys, really appreciate having a sounding board, cuz keeping this all in and not knowing how to handle was tearing me up inside
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