Back to dating, but is he a loser?

iVillage Member
Registered: 01-03-2005
Back to dating, but is he a loser?
5
Tue, 05-01-2007 - 12:14pm

I broke up with my boyfriend of almost 5 years about 5 months ago. I’d usually take a long time to “mourn” a break up, this time I decided not to do that. One of the main reasons is that I’m now 32 y/o and do not want to shut down the opportunity to find true love.
Just a little over a month ago , I met this person online (he replied to my posting). He is 37 y/o, and is an executive at a pretty big company (and this is true because I already googled him to confirm it). According to him, he has never been married and has no kids. We have been seen each other 2-3 times a week. So far, he seems like a very sweet guy. He is attentive. He does not invite me out at the last minute. He took me to a performance and invited me two weeks ahead of time. He has been a true gentleman.

So what’s the problem you may ask? During our third or fourth date, he mentioned that he lived with his sister (who is married and have kids), he also mentioned that his “stuff” are all in storage and that he was in a transitioning period. He said he last lived with a girlfriend about 7 years ago for only a year. He did not volunteer much information. I was able to get this info out of him by asking him directly, but then decided to stop asking because I did not want him to feel uncomfortable with all my questions and I believed he was already feeling uncomfortable.

After that date, I could not stop thinking what he meant by “transitioning period.” On our next date, I asked him point blank why are you living with your sister, are you separated and why are your things in storage? He said that he is actually living with his mother. (I don’t know if I felt worse after he told me that). He said that his lease was up and he decided not to renew it and that his mother was going through a difficult time since the death of his father almost 3 years ago so he decided to move in with her in the meantime until he decides whether to rent again or buy his own place. Well, he has been living with his mom for a year. He picked me up the other day and he had this beat up car from the early 90’s. Yet, he takes me to these fancy places and so far has been spending on me on average $250 per week. I can’t pay for these dinners, but in retribution I cooked him dinner at my house one night.

Here is my dilemma. I’m not shallow and I’m certainly not interested in his money, but I am concerned that what I described above shows that he may have problems managing his finances or that he is just a loser. I am very career oriented and good managing my own money. I bought my home when I was only 26 years old. My mother, who is elderly and disabled, lives with me because I do not earn enough to pay for her rent and my mortgage.

He has this great position and I know for a fact that he makes about 3-4 times my salary. I can’t yet figure out why he still lives with his mom and doesn’t have his own place. I do not think he is married. We have been spending a considerable amount of time together. I paid one of those companies online to find people. His address is listed where he says he lives and only his mother and his deceased father are listed as the additional residents. He seems like a great guy and I enjoy his company very much. I don’t want to screw this up. However, I do not want to get involved with him only to end up heartbroken. Do you think there is something fishy here? Am I just dating a loser? I also think, how are we going to continue dating if no one has a place where we can spend time together alone? I’m already feeling very uncomfortable going out to dinner every week when I can’t pay for these dinners. Thanks for taking the time to read this long posting

iVillage Member
Registered: 05-11-2004
Wed, 05-02-2007 - 11:54pm

Wow....all of those giant red flags but yet he does have some great qualities. I'd be really confused as to what to do too. You don't want to get involved with him if he does have a mountain of "hidden issues" but then again you don't want to pass him up if he is a good guy who just happens to be in a weird spot right now. You are in a tough spot.


I'm not sure I have any ideas or opinions that will help you. I'm as confused as you are about what I would do if it were me. You have already done what I would have suggested, that being a background check.


Could you maybe give yourself some more time to get to know him and his situation? Set yourself a time frame of say 3 months to get to know him.

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iVillage Member
Registered: 05-11-2007
Fri, 06-01-2007 - 9:21am

The fact that he lied about living with his sister at first sent up a HUGE red flag for me. Did you ask him why he told you that at first? Its possible that he was just embarrassed to say he was living with his mother. But lying is one thing I WILL not tolerate. But then again I was involved with a pathological liar who otherwise was a great guy for almost 3 years and eventually I realized that the lying was not going to stop so I got out.

Otherwise he does sound like a great guy. I would do what was suggested and give him some time. Since you already did the background check its quite possible that he is getting his life back together after something happened (possibly a job change or just his decision to help his mother). I wouldn't give up on him completely just yet. And if he is offering ... don't feel guilty about the dinners! Accept them graciously and cook for him occastionally.

Good luck!

iVillage Member
Registered: 11-13-2006
Fri, 06-08-2007 - 5:12am

(doing a favor for cl-fastlaney and visiting while she is away - hence the CL hat)


I smell a rat here. My ex lied to me about many things - I found out later from his friends. I didn't date for close to 10 years because of him.


I was going to suggest the background check, but you covered that base already.


But why would he lie

summer 2010 sig by Tara

iVillage Member
Registered: 11-13-2006
Thu, 07-05-2007 - 5:13pm

Bottom line...

Jilly

iVillage Member
Registered: 01-03-2005
Thu, 07-05-2007 - 8:02pm

Since I posted that message, a lot has happened. First, he asked me to go down the shore with him for Memorial Day Weekend. I agreed, but only for one night and not the whole weekend. We had a great time. Again, he paid for everything. For a moment I thought, this is a guy with whom I can see myself in a relationship.

About a week later, he called and asked me if I wanted to come over. I honestly assumed that if he asked me to come over was because his mother was not home. I was at the mall, dropped everything I was doing and drove to his home. Big mistake! When I called him to tell him I was on my way but needed the apartment number, he sounded as if he was suprised. He said, I have to call you back. 20 minutes later, he called and said he would be waiting for me downstairs. When I got to his building, he got in the back seat of my car and asked me to park the car. When I parked where he said to park he wanted me to seat on the back seat. When I told him no, then he sat in the front passenger seat and began a conversation like he had no intention of going to his place with me. When I asked him point blank if he made me come all the way just to talk in the car, he said no, but that we needed to move the car again because we needed to park in the visitor's parking. When we finally parked, he again began making coversations and did not get out of the car. Over half hour later, I told him that I did not have much time. We went inside the building and just when he opened the door to the apartment, he turned around and said "shhhh", he shut off the lights, and walked me to his room. I could hear the voice of a lady in the background. I assume that was his mother. When we entered the room, I said "don't tell me your mother is here" and he said "what are you talking about" and then left to the bathroom but before he shut off the light and left me in the dark. When he came back he actually had the nerve to ask me to lay down on his bed. He wanted to make out. I left, by the way, I had to leave in the dark because he did not turn on the lights. I felt so cheap and humiliated and I told him exactly how I felt before I left. He said nothing.

I can understand that at the time he called no one was home and that's why he asked me to come over, what I could not and still can't comprehend is why he didn't call me back or told me when I got there that his mother was home and we couldn't come up. Days later, he gave me no excuse, he simply said that he had a few drinks that day and perhaps we should not see each other after he has a few drinks. Quite frankly, I did not smell alcohol on him that night. I think that maybe he was high on something. At this point, I don't know.

I told him that I did not want to see him again. I told him that he is hiding something and that I have no time or patience to discover what it is. I told him that whatever issues he has is something that he has to deal with on his own.

A week later, he called to appologize and wanting me to give him another change, but at this point, the magic is gone.