First Date and Beyond. Is he really interested or keeping you hanging on?

I recently received an e-mail from a young woman who is meeting men on a dating site and with her permission I am publishing it in this post.

"I met a guy on a dating site a while ago. We had dinner. He seemed interested. We had a good exchange and some good laughs. When he walked me to my car I made sure I told him I had a great time. So, he asked me if I wanted to do that again. I said yes. He said he would call.

Five days goes by. Five! He finally e-mailed. Not called, but e-mailed.

“I wanted to write to you earlier in the week but you had hidden your profile. I really enjoyed our date (though I'm still not sure if I was just the Monday menu or you are actually interested in seeing more of each other. You are very intelligent and quite charming and funny. If you would like to see each other again, just let me know.”

I write back:

“I am actually interested in seeing more of each other. I know guys have this three day calling rule, but disregarding it, please give me a call sometime.”

He writes back:

“I did think you weren't interested or I would have called earlier so I will give you a call today.”

He called back the following day. Here is the conversation:

He: “Hi, I was wondering if I could see you again.”
Me: “Sure, I would love to.”
He: “Are you sure?”
Me: “Of course!”
He: “I wasn’t sure if you were interested, or I would have called you sooner.”
Me: “Of course I am interested. I told you that.”
He: “Ok, let me figure out my schedule and I’ll give you a call tomorrow to set something up.”
Me: “Sounds good”

The following day, sure enough, he doesn’t call.
Not that I sit and wait. I figure out, this is kind of strange, but who knows what happened. Perhaps he is not all that interested or maybe he is having problems with his psycho ex-girlfriend. Again. Not my business to sit and analyze why he is not calling. Big deal! It was merely a first date.

A month goes by. He e-mails me again.
“Have you found anyone yet or are you just setting up dinner dates still? I enjoyed our date and one of these days would like to see you again but I've been really working hard.”

That starts getting annoying. Enough already! Fine, I write back:
“Considering the drive you may want to come out Saturday evening. I still have it open. Please, let me know fast, those spots fill up quickly.”

That was on Monday. He responds on Wednesday:
“Well if I do I can't drink more than one glass of anything. I was so tired last time that I was falling asleep at the wheel on the way home.”
What is that about? He approached me on a dating site, knowing that I live two hours away from where he lives. He was the one to maintain that the distance would not have been a problem. By the time he wrote to me I had already made plans, so I informed him of that.

He writes back:
“Well, if you're actually interested in seeing more of me (as in I'd hate just to be filler on the social schedule) let me know. You are a lot of fun to be around I think.”

This gets me more and more annoyed. But I don’t want to be snappy or rude. He actually seemed like a nice guy, but I just don’t understand his hesitation. He either wants to see me or he doesn’t. I respond: “I told you I wanted to see more of you, but you don't seem too motivated.” His response: “Sorry about not seeming too motivated. I do like you, but you shook my hand so formally at our date that I really didn't think you were interested at all. When you said you were interested in seeing me more I didn't really think you were. We are too far apart for me to waste both our time unless you are actually very interested in me. I rarely show how attracted I am to someone (so I'm told) though I think that it's really obvious.”

Me: “I like people with perseverance which you show lack of. Girls don't sit and wait for a dude to call. They move on. If a dude doesn't call early in the week, chances are she will get booked. I told you I was interested. What else do you want me to say? Do you anticipate love confession on the first date?”

Then she e-mailed me. Here is my response below.

“This sounds to me like he wants to keep you hanging just in case. Don’t you sometimes do it when you don’t really have strong chemistry with a man, but want to keep him around just in case nothing better comes up and you don’t want to end up without a date on a Friday night? Sounds to me like while he is dating other girls, he may be unsure if there is anyone he may be interested in and while it doesn’t sound like he is head over heels in love with you, he is still considering you as an option No.2

I am not sure if this is the position you want to be. It’s your call. But I suggest that if he doesn’t stop dragging this out right now, cut him off and do not respond until he actually calls you or e-mails you with a firm date and time for a second date.

On the other hand, he may have self-esteem problems, emotional baggage, insecuries and such. In any case, it sounds like it has been too long and you have said numerous times that you were interested in him, so he should not feel intimidated.”