Hi bill is someone I know at work, and he's terrible at this dating thing, so I offered to help him the only problem is I think I might be in over my head. First I'll give you some background information then I’ll tell you my plan

Background

It all started when I caught bill giving a Valentine’s letter to a seventeen-year-old girl don't worry he wanted her to hand to a twenty-year-old who is smoking hot. Cute right well it’s not he's thirty. I told bill no man should send a girl to speak for him. I said to him you have to give that to her personally. He took the letter and prepared to do the deed. Not going to lie I knew he was heading for disaster, but I thought this would help him grow.

Later that night

My boss was counting my tips I'm a (bartender), and she asked me to stop Bill from giving that girl the letter. She explained that this thing was going to make the girl in question uncomfortable at work. I felt terrible for encouraging Bill, so I agreed to stop him. I sent Bill a text warning him that the girl in question had a man, but I promised him id teach him how meet women and help him lose his V card.

I'm worried Bill might be nuts tho my boss told me they had to sit him and tell him to stop inviting women out to strip clubs

He's here's how he stacks up not being mean just being objective

  • he's short
  • got a belly
  • doesn't take care of his skin
  • low social skills
  • works a dead end job at 30
  • he knows how to party
  • goofy guy
  • doesn't take himself to seriously
  • willing to learn
  • decent human being
  • I could see a nerdy girl digging his style

Here's the plan

Phase one

Teach him to stop talking about strip clubs with women and forbid him from going after girls at work. I'm going to try and teach him how to hold a conversation. Tell him to stop telling girls he's a virgin. Take him to meet up were he can make some friends that girls so he can take them off the pedestal and treat them like people.

Phase two

I'm gonna try helping him with his confidence problems. This might be fucked up for me to say this, but I might have to convince him to lower his standards dramatically.

Phase 3

Once he starts showing signs of progress, I intend to take him to countless speed dating events until he feels like he doesn't need my help another more.

I need help though I'm not some magic matchmaker I'm just a dude with decent dating experience and to be honest I don't have to work as hard for the attention of women as other guys.

Question one should I mind my own business? Question two does this sound hopeless to you? Question three do you think my plan is good? Question four how would you help Bill?