And if so how did it work out?
You always see TV sitcoms and it’s a staple of the sitcom format. Someone plays matchmaker with typical hillarious results.
But what about real life?
Have you played the matchmatker? If so was it good? Bad? A disaster? Or did it have hillarious results? 
Just the once. Several friends were planning a New Year’s outing to a performance, with a dance afterwards. I was set up on a semi blind date with a guy for the evening. It was a nice time, but at the dance part it became apparent that he knew how to dance properly. So when I went home, I told my roommate–who loved to go out dancing properly–that she should go out with him. She introduced herself, they went dancing, and now they’ve been married for 16 years and have 3 kids.
Yes. Two friends who thought they were friends but were clearly both in love with the other. He was single, she was in the lingering dying phase of a fairly long relationship. Many an evening on the patio counselling “dump the jerk and jump S” finally resulted in a 7 year marriage of the two people with the best matched weirdness in the world.
Accidentally. Years ago, my brother was visiting me at the university I attended. I intoduced him to a bunch of my new friends and acquaintances. My brother took one look at an acquaintance’s massive rack, and fell seriously in lust. They married a few months later. It was a disaster.
Actually, though, I have two long-time friends for whom I’m dying to play matchmaker. They’d be perfect for one another. But then I think back to my brother’s marriage, and think “I never, ever want to be blamed for a trainwreck like that again,” and come to my senses.
I don’t know if this counts as Matchmaker. It certainly counts as Introducer.
Labor Day weekend, 2009. Friday night services in a community group I run (along with some other people).
A young lady was attending for her first time. As we were leaving the service, I introduced myself. We talked about leading services, and using nonstandard melodies. She said she sometimes did the closing hymn to the Hobbit theme from the Lord of the Rings movies.
I suddenly turned around and grabbed the attention of a friend, who I knew to be a major LotR movie fan. I then said “Hey {friend}, you’ve got to listen to this.” Then I had the young lady sing the hymn with that melody. (Yes, I was very direct, blunt, and putting her on the spot.)
The two of them had a good discussion all through dinner. June 2010, they announced their engagement. Their wedding is this November. 
He says he owes me a major favor. I owe my rabbi a major favor for introducing me to my fiancee. So logically, if he introduces one of the rabbi’s children to their future spouse, the circle will be complete.
Yes, and it ended poorly. It was between my boss and my boyfriend’s brother. On the whole it seemed like a great idea and I thought the two of them would really click! But apparently he has the “I’m an average guy who deserves a supermodel” mentality thing going on, and she was kinda crushed about it. She’s not ugly, a tad on the plain side but otherwise nothing really wrong with her, while he on the other hand… well… Let’s just say I’m glad I got the brother I did, mkay? They hung out twice, once being a double date with my boyfriend and myself, and then he announced that she wasn’t “fun” enough for him. Coming from the guy who sits at home… with his parents… doing nothing… But apparently he told my boyfriend that he didn’t think she was pretty enough. Of course I didn’t tell her this, but damn! Can you get any more shallow?? No worries, she went on eHarmony shortly after and found a pretty great guy!
When I worked at a summer camp, I had two friends (one English, one Scottish) they were always mooning over the other to me but shy. So every time one would say “ohh, she’s sooo pretty” I would be like, “ask her out” and the other would say “oooh, he said the funniest thing today” I would be like, “ask him out.” Without saying that the other had spoken to me.
Anyway, they’ve been married like 10 years now, and have two kids. I don’t think of it as matchmaking per se, more like I brokered the deal. They were just being too British about and needed a good American shove in the right direction.
Yes, when I moderated a message board. A good friend (A) who was also a member told me that he liked the posts by a particular guy (B)and was quite excited about meeting him at a forum meet.
After the meet up, B pm’d me to tell me what a great time he’d had, and mentioned how much he’d enjoyed meeting A.
A also pm’d me to say how great it had been to meet **B **but he’d been too shy to ask him out at the time. I told him that I was pretty sure that B fancied A and A should take the plunge and ask him out.
They lived together for about seven years but sadly their relationship ended about a year ago.
Only once. My husband and I were at a bar some years ago hanging out with some people he kind-of knew from work. We were playing darts with a guy who I knew immediately would be perfect for my sister (who was not there), so I convinced them both to go on a double date with us. They ended up dating for two years.
Yes. A friend of mine wanted to meet my sister’s best girl friend, who was living with us at our family home, after high school. I mentioned this to her and she said, “isn’t he weird?”, I said “no”, so they went on a date.
I don’t recall if she ever did come back home, if she did it wasn’t for long.
That was over 30 years ago and they are grandparents now.
I have too and it’s another success story. She was a friend of mine who had been in an LTR that had gone sour when he had an affair and after that her attempts at dating seemed to not be working out (I don’t know why she was so surprised to find out that good looking men tend not to want to have long term relationships). This was starting to get her down and as she’s very attractive herself was starting to feel like she was the person people sleep with a few times and move on from but not actually settle down with. So I’d been keeping an eye out for someone nice for her, and definitely wouldn’t let someone I didn’t think was right upset her any more.
He was the flatmate of a friend of mine from my dance class. I’d bet him a few times and he seemed really nice so eventually we did the big group drinks thing and I gently steered them together. They’ve now been married for three years and have two children. I keep threatening to actually call in the dowry that I’m owed for getting them together but I just don’t have the heart to.
Yeah, two people I used to work with. I was good friends with both of them, and they were clearly falling for each other but wouldn’t do anything about it, so I gave them both a stern talking to. They’ve been together for about eight years now, married for four, and have two children.
Does it count if I steered someone towards online dating? He did, due to my coaxing him on, taking pics, etc, and he got married.
You could just have a party and invite both of them. That’s what I do, ever since a couple I introduced ended badly back in the 1980s.
Unfortunately, the two of them live a fair distance away from one another. Maybe I can convince H to come visit, and arrange a casual meeting with J while she’s here… Or maybe two 41-year-old, never-married, very religious accountants are just destined to remain single!
I made my shy friend talk to my other friend last year. He had mentioned he thought she was beautiful and I cornered them both into conversation knowing what a great match they would be. Theyre currently planning their wedding… and as a floral designer I am very excited to be doing their flowers!
Once. They were married in less than a year.
Mrs. Tildrum and I were set up by friends.
I inadvertently brought together two friends. They were both in my online community (which was an extension of the SDMB, actually - neither of them post here anymore, though) but I think I was the only person they were both friends with. I regularly chatted with one of them in the old irc chatroom, and convinced the other to come to the chatroom, not to set them up, but because I thought she would enjoy it. It turned out they had a mutual geeky interest, and started chatting privately about it.
They kept their relationship secret for a long time, though. I certainly had no idea about it until they’d already had a chance to meet in person and decide that they really did like each other.
They’ve been married for six years now.