How do I do this?

I really think you ought not involve yourself in your sister’s environment.

Please back off.

You are quite capable of finding romantic prospects in other places.

I disagree with Punkey. Life is for living. I would say, ask him for coffee. If an attractive woman invites me for coffee... I am in!

Not lame at all.

Whilst I think that the theory is ok I would advise not doing so. I see that "most of your money comes from the sex industry' that may well be something that would not be seen as good!! The only way it would work is if he was cool with it. Speaking for myself I would not want anyone I was "involved with" working in the sex industry in any way. I would however complement you on doing your best outside that industry to keep money coming in! My s/o who is as of today polyamourous & that is not cool in any way shape or form. She also does drugs which is a big NO NO for me, the only ones I do are prescribed & most of the time I never take those at all.

I was not saying she was not a nice person. I did give her complements but ask yourself if you would want to be in a relationship with a sex worker?

That is your hangup, not mine. I choose my relationships by whether I have like being around with them, whether they are fun and challenging and decent and make me feel happy.

I wouldn't want to be in a relationship with a judgmental jerk.

So (depending on what she does) you would be happy with someone dating/sleeping etc with other people & with the risk of catching a disease etc. For me that would be a big NO No but its your choice!

Listen to yourself.

You are saying that a a sex worker, in your eyes, is unworthy of pursuing a loving relationship. That is bullshit. People are people and we all have our different lives. I do not think your prejudice is valid at all.

You are showing no regards for the feelings of the person who started this thread, a real person who has done nothing to hurt you. She didn't ask you for your asinine judgement of her life. She was only asking about whether she should ask someone she likes to have a cup of coffee with her.

I would be delighted if the OP asked me for coffee.

I hold no bad feelings towards her at all!! MY point which you seem to be completely missing is as a potential partner & this is the key point is about dating a worker from the sex industry?? If she is only asking about going out for a coffee that's great but when/if you take it deeper that's another matter!

That is your hangup. That doesn't mean that everyone has that hangup. Everyone you meet has something in their life; when two people start a relationship they either work these things out or they don't. If you don't want to date someone, fine that is your decision. Don't put your garbage on anyone else.

To judge someone this way is asinine.

What happened with the woman at the library you wanted to go out with?

https://able2know.org/topic/450489-1#post-6611378

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In any case, I agree with Punkey on this (which is truly a rare thing when it comes to relationships ) . Try to leave the school a cool place for your little sister. A family member dating school staff? Uncool for the child at the school. Based on your posts, you and your sister have both been through a lot. Let the school be her place.

There are a lot of nice people out in the world who aren't part of your sister's immediate world. Go to a coffee shop - go to a concert in a park - go back to the library . Meet nice people out there.

You might want to take your issues to a thread of your own.

Spreading them all over Jessie's thread really isn't helpful to her or her sister.

I'm kinda with all of you, and I do see everyones point. As much as I want to go out with him, I think it is better if I leave in my fantasy land. My little sister likes him and trusts him. I don't want to mess that up. She finally has someone she can talk to, and I don't want to mess that up. But I agree, some guys have real hang ups on this. I've gotten used to being that dirty little secret in guys lives. To be hidden away except for fun.

The woman from the library, sadly, I've never seen her again.