<human>: Hello people of reddit. So I'll get straight  to the point. No one involved really reddits but I'll give them fake names for privacy sake.

Anna: one of my closest friends from high school. We went to different cities for university but we stayed close. We are back in our home town and are hanging out a couple times a month. 

Tom: a friend I met in university. I met my boyfriend through him ( he did not exactly set us up, my bf was one of his roommates and he hosted movie and games nights)

Tom has just moved to my home town. We are hanging out with him regularly as well.

My question:

Tom has been single for a while since he broke up with his ex. He is not a big fan of online dating and has had little success. Anna is also so gle and has lately been telling me how she wishes shed meet someone soon. 

I think Anna and Tom could potentially be a good match. They share a lot of interests. And I happen to know they would both find eachother attractive since I know  their type. 

I was thinking of setting them up some how and expressed my idea to my bf. He is against it. He says setting people up is a bad idea. If it works you rarely get thanks. If it doesn't it blows up in your face.

He is worried we could lose friends and cause a lot of drama and head ache potentially. 

So people of reddit. What is your experience? Any ideas? I was considering creating the ground Tom did when I met my bf. Inviting Anna and Tom over at the same time see how things go. Or should I be a bot more direct and express to them I think they would be a good match? 
Should I just stay oit of it all together? Have you ever set anyone up? Both positive and negative personal experience  would be appreciated.

Can you provide a brief rundown of the text in within 3 sentences?
<bot>: thinking of setting up two og my close friends who have never met eachother. Bf says it's not a good idea. What do you think?