We get a lot of advice questions coming in at EMandLO.com, but sadly, we just can’t answer them all. Which is why, once a week, we turn to you to decide how best to advise a reader. Make your call on the letter below by leaving your advice in the comments section. 

Dear Em & Lo,

I have been on and off with my boyfriend for close to four years. On our first go, we were together for almost a year and broke up because of a MFF threesome we tried. It was absolutely terrible. She was one of his family friends, she had more of an interest in having sex with him solo than she did participating in our arrangement. She wouldn’t leave after, wouldn’t stop trying to contact him to pursue him, and no matter what reassurance he gave me that he wanted nothing else to do with her, I couldn’t leave it alone and we eventually broke up. After getting back together years later, he admitted his faults, said if he would’ve known how our relationship would’ve failed, we wouldn’t have done it. It was rushed in planning, and it was rushed in the life of our relationship, and we both now see the errors in the whole situation, my jealousy (even tho I totally condoned it), and him pushing the whole thing so quickly after getting the greenlight (men) without a lot of feedback from me and what and how I wanted things.

We have been back together for almost a year now, and are poking at the idea of trying again. Trust me, it’s  NO WHERE in the near future! The thing is, we went from not discussing “the incident” to being openly candid about our feelings on what happened. Actually having a good threesome experience is on both of our bucket lists, but we know right now that our relationship is no where near ready for something like that. 

My question is, how can we eventually try again without it completely ruining our relationship, if and when that time comes? I know that total trust and communication is needed, and it’s there, but what other tips are there to assure smooth sailing before, during, and after something that we both want to be a fun and exciting experience? Thanks.

xo,

Threesome Thoughtful

What should T.T. do? Let her know in the comments below.