Where Do We Draw the Line for Being Too Nice?

preying on you

Have you ever had a friend so generous that they would give you the shirt off of someone else’s back? You know, one of those people who is always happy to help at the expense of another? I have a friend/colleague who is just like that…let’s say his name is “Dan” to protect his identity. Dan and I have known each other for about 15 months or so. It took me a long time to gain any trust for Dan because I felt from the beginning that he was taking advantage of me. It seemed clear the day we signed a lease for an office space for our business, which he agreed to run for us.

Dan is very close with his family, specifically his oldest brother and mother, who all live together. They were all together when my wife and I showed up at the office to meet with the building manager and review the lease. Confused as to why there was a posse of people waiting for us to seal the deal on the office, we rolled with it as best as we could. After signing the documents and handing the check to the property manager, we invited the group to join us for a celebratory lunch for our new venture. We met at a casual tiki bar along the water to sip some wine and enjoy some Caribbean food.

We arrived first with Dan’s group a few minutes behind us. When they sat down I thanked them for joining us, and his mother replied, “Dan was going to take us home but I told him that you invited all of us so we were going!” Don’t get me wrong, she was pleasant and wasn’t trying to be rude, but it made me start to analyze the thought process. The bottom line was that we did invite them and the gesture was certainly sincere, but when you get response that doesn’t feel like gratitude but more of a feeling of “I knew you were paying so of course I was showing up to eat!”, it makes you cock an eyebrow…at least it did for me and my wife. Not to mention that Dan and his brother acknowledged that they don’t normally drink wine but thought they would have some that day since we were already celebrating. Regardless of my mind wondering whether or not I just made a mistake inviting this man to represent our company, the lunch was quite enjoyable and the weather was perfect.

As we finished lunch and continued to enjoy some wine, Dan, holding the menu in his hand called the waitress over to answer a few questions about some specific items. We couldn’t hear the conversation over the music and since the rest of us were in discussion and nobody was paying attention anyway. Then it all started to come together. After pouring some more wine into mine and my wife’s glasses, I put the bottle down on the table and Dan quickly picked it up to examine how much was left. He kind of mumbled something about not being enough wine left, which was confusing to me since he had barely drank anything that was already in his glass. Unable to understand what he was trying to say, I asked him what the problem was and he then notified me that his lady friend, whom we had never met before, was joining us for lunch. Apparently his unexpected guest was also a fan of red wine, so he wanted to be sure there was enough to accommodate her, hence the need to order another bottle. Oh, and that little conversation with the waitress was Dan ordering his girlfriend’s lunch, which was timed perfectly since the food was ready in time for the arrival of our unknown guest.

Despite feeling like I just got mugged in public, I did my best to keep my composure while Dan’s girlfriend finished eating her lunch and drinking her wine. What’s worse is that this woman was not pleasant at all, almost to the point of being rude. I could feel my wife’s energy as she sat next to me, and after 13 years together we can practically read each other’s thoughts in these situations. Except my wife wears her emotions on her sleeve and is still struggling with the concept of the poker face. Actually, as I am writing this I remembered the text messages we exchanged at the table so I pasted it below…LOL!

moocher So, we made it through lunch and had plenty to talk about during our trip home. About a month after renting the office I was approached by the property manager regarding Dan. She informed me about a complaint from one of the receptionist staff, a young female, who felt that Dan had made some inappropriate comments to her. This was certainly not a good representation of our business, and a huge potential liability, especially with Dan being a 41-year old man. To save our reputation in the building I addressed the situation head-on with all parties so it didn’t escalate. Fortunately they acknowledged that the receptionist could have taken things out of context, but we still weren’t convinced that Dan was innocent either. He seemed to be spending more time in the business of the other tenants than actually bringing in clients for our company as he had promised.

In the months ahead I was never bashful about telling Dan what was on my mind. I didn’t feel that his performance was up to speed and I let him know. When I thought he might be using my office for personal business I let him know. When he asked for advances on commissions I reminded him of our investment in him and told him he didn’t deserve it. I beat up Dan whenever I thought he deserved it and that was often. I thought he would have walked out for sure but he had a thick skin. I began to respect him more because he knew I didn’t trust him and I made it clear, but he still wanted to win me over. As we began working together on other projects Dan’s contribution improved. He brought ideas and people to the table that could help us in some other business ventures we began working on. He started to prove his dependability and loyalty, which meant a lot to me. We could always count on Dan to check our mail when we travel, make bank deposits, and handle other helpful tasks for us. He really earned his trust with us after a very rocky start. I consider him to be a good friend.

So, let’s fast-forward to last Friday, August 29th, the start of Labor-Day Weekend. Dan called me at around 4:30pm. We speak nearly every day and several times on certain days. We frequently share new ideas or situations that have occurred to see what opportunities can arise from it. He generally brings the people and ideas to the table and I handle the execution. He was so excited when I answered the phone and was talking fast and it took me a second to even comprehend where it all was going…

“Bro, bro…do you have a cape handy? And your shirt with the “S” on the chest, is that folded up and ready to go? I can get it out of the dry cleaners for you!”

Still not sure what the heck this guy was talking about I tried to hear him out. Between being caught off guard and his fast speak, I wasn’t sure what he was asking me to do until I heard him say, “Hey you don’t know if you don’t ask, right?”

He proceeded to tell me a story about his current girlfriend, let’s call her, “Jane”, who we met once a few months earlier. He asked if she could stay with us for a short time because she had to be out of her apartment in 3 days (at the end of the month) and the new apartment won’t be ready by the first because it didn’t pass the requirements for the government subsidized housing. Still trying to wrap my head around his whole Superman analogy and excitement as if I had won the lottery or something, I was speechless. Trying to keep my composure and fully comprehend the request, I said, “Ok, what exactly is the situation with Jane’s apartment?” Dan jumped in, “Let me just put her on 3-way and she can explain it to you.” Now he was pissing me off. “No Dan, don’t put her on the phone. I need to discuss this with my wife first. Give me a little while and I’ll get back to you.” Baffled at the request I just needed to get him off of the phone to sort it all out.

My wife overheard some of the phone conversation and I filled her in on the details. Despite our online presence and marketing for our businesses, we are extremely private people when it comes to our personal life. Outside of our local neighbors, we can count the number of people who know where we live on one hand because our property (houses, vehicles, etc.) are in trusts and we use private mailboxes. That’s just the way we are, we don’t like unexpected visitors and truly enjoy our privacy. Dan is very aware of this, and unfortunately in our experience with Jane we’ve found that she is quite the opposite. She likes to post selfies online at every opportunity and share lots of details about where she is and what she is doing. Not to mention her career-criminal, a 6’3″ 260-lb ex-boyfriend, who she has a restraining order against for calling her over 700 times in one month! Yes, could we please have that drama and nonsense come into our lives? We really appreciate that, Dan!

In speaking with my wife in more detail we just were not comfortable with Jane staying with us. It had nothing to do with her as a person, since my wife and Jane were friendly and kept in touch after meeting that one time. However, that doesn’t mean that we wanted her under our roof! We felt as if we were being put on the spot which made us both anxious. As promised I called Dan back to try and understand the details more clearly and how long it would be for. When I asked for specific details again to make my wife aware, Dan replied, “That’s why I wanted to put Jane on the phone with you earlier to explain everything.” Trying to keep my head from flying off of my body, I barked back, “I know Dan, but I don’t appreciate you putting me on the spot like that! I told you I wanted to speak to my wife, so show some respect!” Despite my frustration I allowed Dan to put Jane on the phone, but the details were still a bit vague since they didn’t have exact dates as to how long the situation would take to resolve. What I took out of the conversation was that it could be a few days but wouldn’t be more than a few weeks!

We reluctantly agreed but didn’t feel good about it at all. We both had a pit in our stomach from this and felt pressured. A few hours later I would receive a call from my friend Egedio…who I just refer to as “G”. G is one of my closest friends and much like a big brother to me. My wife adores G as well and we both respect his opinion highly. He met Dan before and said what many of you are probably thinking…”Why can’t Dan put his girl up in his place?” That would be the obvious question but Jane lives about an hour North of Dan and was much closer to us making it more convenient…for who though?

G went on to say, “Dan’s driving that nice Cadillac with the automatic starter but we can’t spring for a hotel for his girl for a few nights? Listen, you guys are too nice and that’s why you are feeling this way. Just say “no” so you can feel better and get back to your life.” This made all of the sense in the world…none of us should have to do anything we are not comfortable with and I needed him to be our voice of reason. He even offered the same idea that I had which was to pay for her to stay at a hotel for a few nights. I know, it’s not my problem but we were still in the off-season for Florida and the hotel rates were very reasonable. I figured spending a few hundred dollars to save a whole lot of headaches would be money well spent…and G agreed.

With Egedio’s advice resonating well with me, I called Dan and explained that we couldn’t help out but offered the hotel idea. It turned out not to be necessary, and while Dan seemed fine with everything I still have the feeling that he just doesn’t get it. Don’t get me wrong, I don’t care if he truly understands or not, but the question I have is…

In your opinion, do I still keep Dan around or is he someone I should keep at a distance or consider editing from my life?