Letting Someone Else Set Up a Date

Okay so I have been single for close to five years now my problem is I am too socially awkward to go somewhere and randomly strike up conversation with people. A friend of my mine (who really is a brother to me really) told about this person who he thinks would be a good match for me. I just don't know this person also works with him and while I appreciate the offer I don't know what to do the possibilites are too much either it works out fantastic or he stuck his neck out and it starts something affecting his work. I want to take him up on it but my brain is saying that I would risk too much on someone else to do so. Does anyone have any advice on having someone else set up a date before?

Most date set ups by friends are pretty crappy. I've gone on a couple of dates set up by friends trying to be match makers or just "think you two would be great together". Honestly those were probably the worst dates I have ever gone on. Your friends/family may think someone is right for you, but when you two get together you think to yourself "wtf were they thinking!".

Remember the one I asked my friend afterwards, "where the heck did you even find this guy? He's such an asshole!" And she replied "well you both were Christian, I figured it would just work out?" (-_-)

The other one my friend slept with him since they apparently had history she never told me about and he called me wanting to do a 3-some without her knowing till it "happened". Told him to fuck off and have a nice life (^_^)b

If you decide to give something like this a shot I would say go out in a group like social setting. Don't let your friend set this up as a one on one date till you get to know this person better. If this isn't possible then you decide if you want to do this or not. I can't say all set up dates are shitty, but again having an inexperienced person decide what kind of person is good for you doesn't normally end well. This friend also doesn't seem to realize if this date goes poorly that this could affect his work relationship with this person.

My personal opinion is to say no, but my advice is to really just think this through and decide for yourself if you wish to do this or not. I can only tell from personal experience and some friend told stories how this isn't the greatest, but I'm only one opinion lol.

I'd say go as a double date.(I'm assuming he's attached). This is best if you're socially awkward. Go, be yourself, be confident, talk to her/be interesting, let your friends fill in the conversation lulls(when you're socially awkward/regrouping your courage). If you go, and one of you doesn't like the other then at the least everyone had a fun night out and you got some practice to get back into things. Unless she's really immature it won't affect their(your friend/her) working relationship. If you trust his judgement enough to pick a possible mate for you, I'm guessing you trust it enough for him to judge her mature enough for that.

The only failure in this situation is not trying.

Just go to a group event, like a party or whatever. Have your friend introduce you to co-worker and see if you two hit it off. No need to have a "date" right away anyways.

Honestly I would do it if I was you, but I would also make sure it was something small and non committal. In fact I would even bring this up with the person trying to hook you up. Mention to them that you would rather just hang out then date because you just want to see what the person is like.

I have one pre set date and it was awful...
I say give it a chance. Dating hard but maybe at least thing could give perspective on dating since its been a while.

No one has ever tried setting me up, I can't imagine there's many positive things to say about me to someone else.
I'm a bad date waiting to happen, all my dates have been bad.

This sounds like a toughy. If your friend knows you pretty well, and you trust him to do right by you, then I don't see what you stand to lose by giving it a go. Maybe try asking to be introduced to her in a casual setting to get to know her a bit and just be super clear that it's not a date-date, if that makes a lick of sense, ;p