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female
age
41-50,
anonymous
writes: Hello,My problem is the following: I'm scared to death of entering a new relationship, or rather, scared to death of messing up a new prospect. I am a professional, financially secure 31 year old woman who lives in New York. Not 21 anymore, but middle aged I guess by New York City dating standards. Some options have been foreclosed, but some remain.I met a man four weeks ago at a Museum event. He is 47, very wealthy, and has an incredible job title. He is divorced and has two kids, 9 and 11. Me, I have never been married and have no kids. The man, "R" also looks much younger than his age (I thought he was in his late 30s/young 40s when I met him.) Frankly, after I got his business card and Googled him, I was surprised that he was even talking to me. His background and status are extremely impressive.When I first met him, I took his business card, but didn't have one on me, so it was up to me to make first contact. What he said at the time was, "Give me a call sometime, maybe we can go look at some art." So I e-mailed him a couple of days later. No response from him a couple of days later. So then I did something that I was kicking myself for immediately - - I followed up the unrequited e-mail with a phone call. Immediately, I felt like the situation was doomed. I had called on a moment of impulse, and plus the voicemail was rambling, so I thought it was now a lost cause. That was a Friday evening.Much to my surprise, his administrative assistant called my office the following Wednesday telling me that R was in a meeting but she had received my voicemail. The next evening, a Thursday, R called and left me a voicemail. By this time, I was just shocked that he was getting back to me. And I was overwhelmed by the whole thing, plus it was a very busy time (professionally and otherwise) so I didn't get back to him. It was by no means a strategic move, just the way things turned out. But sure enough, and even more to my surprise, he called back that following Monday. We talked for about half an hour and it was a good conversation. HE actually sounded nervous (asked a lot of questions, voice was high pitched at times, etc.) We left the conversation with him telling me to give him a call back so we can set something up. I called him back three days later on that Thurs. and left a voicemail. He texted me that evening asking me if I would like to attend a jazz concert the next day at Lincoln Center. I texted him back saying that I would be unable to attend (my office holiday party was that evening) but that I like jazz. I attempted to be a little flirtatious, so he wouldn't think that I was disinterested. He said, "Next time." I texted him that next Monday to find out how the concert went and he said great. Turns out he has season's tickets. So I was a little torn. It was a nice invitation, but on the other hand, (1) he texted it to me, (2) it was for the very next day, and (3) he had season's tickets anyway. Who's to say that he didn't call someone else right after me to see if they wouldn't be available instead? So after my text about the concert, we played phone tag for the next couple of days. Finally, two days later, on that Wednesday, we caught up to each other. This second conversation was more strained than the first one. Moreover, he sounded much more laid back, detached and disinterested than he had in our first conversation. The conversation itself didn't flow as well, and I felt like I was the one being a little high pitched and asking more questions this time. It ended with him saying that we should talk again later and with him saying, "Happy Holidays!" I then asked him if there was a good time of the day to reach him. He said no, it just depends on when you catch him, and that I could feel free to call his buseiness number. I didn't feel as if the way we left off was very encouraging at all. And plus, he said the Happy Holiadys thing last Wednesday. Considering the timing, that could mean about two weeks before I spoke to him again. So I felt very anxious and uncomfortable after that conversation, and like I didn't know what to make of our status. I decided it would be best to leave things off on a good note until we spoke again, so the next morning, I texted him that I enjoyed our conversation and that we should get together when things slowed down after the holidays. He wrote back, "Sounds like a plan. Happy Holidays!!" I wrote back, "Happy holidays to you as well." I then proceeded to erase all of his phone numbers and information. I felt that I had shown enough interest at that point, and if he was interested, he would eventually call again. My fear is that I may have overcompensated for that initial rejection of his date offer. I didn't want him to feel that I was disinterested and aloof, but on the other hand, I don't want to seem too eager. With the last text that I sent him, I figured that if he has any doubt that I'm interested, they should be allayed. Now it's his turn to do all the work. That was last Thursday, this is a week later and I haven't heard from him, as I suspected I wouldn't. If I haven't heard from him by this time next week, I guess that'll answer all of my questions as to whether or not he's interested. So what are your thoughts from what I've told you? Is he interested? How much? Were the things he said in the last conversation a clear indication that he is no longer interested (or not as much)? Have I showed too much interest toward him? Have my actions up to this point been appropriate? Your help is much appreciated.Thank you.
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reader, anonymous, writes (29 December 2006): Good luck with asking him out, I think he will go, why not you made him a bit shy before and that is a good sign. As far as the Christmas Party and introducing him to your co-workers, I guess it depends on how formal your workplace is, but I would have just introduced him as a friend, not a beau...if your co-workers ever meet for Happy Hour, that also is a great place to invite him because it is casual and he can see how you interact with your friends, and you can see how he behaves as well, sort of relaxed and no pressure kind of thing, not a full on date where you feel like you are on a job interview!
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reader, anonymous, writes (29 December 2006): This is verified as being by the original poster of the questionThanks R & B. Your answer was very helpful. I view him as a great prospect, and I guess that's why it's hard to be as relaxed as I'd like to be. But I know that I have to lighten up a bit, and that will help things go smoother. To answer your question, it didn't occur to me to invite him to my office holiday party. Besides, guests were not allowed. Also, wouldn't it be too soon to introduce him or any new beau to my co-workers? But if he doesn't call again, I'll take your advice and give it one last try... an invitation a couple of weeks from now to get drinks or coffee. If that doesn't work, then I guess it wasn't meant to be.
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reader, anonymous, writes (29 December 2006): Well it sounds like he was interested, but maybe the whole thing lost some momentum when an actual get together did not happen, can I ask why did you not ask him to your holiday party instead of the jazz concert, explaining that you felt you had to make an appearance? I think if you don't hear from him in a week or so call him up and then nail a date and a time to get together, don't ask him to a scheduled event ask him when he can meet you for lunch or coffee or dinner or what ever you can think of that has a flexible schedule, if you don't meet then things can't move forward, I don't think as adults we need to play hard to get, but you just don't want to be too open book and intimate right off the bat in conversation, lighten up, don't try to impress so hard and just smile and have some fun, listen mostly to what he has to say to you when you do get together....hope you get a second chance! I live in a smallish town, but used to live in Dallas, and life is much faster paced in the big city and people are busy and they have lots of opportunity to meet people, so you have to be more assertive, better organized and just go for it because if it does not work out, there will be someone else down the road to meet....
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