Real stories about dating and relationships in New York City. Truth is more interesting than fiction.

Is Hope Bad?

I had a last night. Really good.

We first connected online a few weeks ago. I winked at him. Yeah, I know, are cheap and pathetic. It’s not that I’m too cheap to send a message (I’m currently using a site that has a pay per message plan. I promise to dedicate several future entries to the different dating sites and their pros and cons.). I’m just tired of making the effort of writing a message only to be ignored. I don’t take it personally. I don’t think it has anything to do with me. I’m a strong, quirky, 38 yr old woman looking for a . Lots of guys aren’t interested in any of those things regardless of what they say in their profile.

Anyway, I winked and he immediately sent me a message and then we exchanged a couple of messages and were going to meet but had scheduling issues. The next thing I knew I got an email from him telling me he was going out of town for a few weeks but he’d love to get together when he got back. I figured I’d never hear from him again.

But I did. Last week he sent me an email saying he would be returning this week and we made plans for drinks last night after work. It was, by far, the best date I’ve had in months. I don’t want to jinx it by giving away too many details but we did kiss and it was sweet, almost too sweet, but it was a first date and we’re just feeling each other out, I figure.

There was an email from him waiting for me when I got home last night, telling me how much he enjoyed meeting me and that he’d like to see me again soon. I replied positively. So here’s the thing – am I allowed to ? I’ve been here before, so many times. Just a few weeks ago a guy asked me out for second date, I said yes despite the fact that I had serious concerns about him as a potential BF (I’m trying to be open) and then he emailed me the night before our date telling me that he needed to go out of town for an emergency business trip and had to reschedule. He never rescheduled (and I’ve seen him trolling the dating site since).

It’s probably too early to be hopeful about last night’s guy. I know that. And heck, I have a 2nd date with someone else tomorrow night. But when can I hope? After our second date? Third? After we start having mind-blowing sex? I just don’t want to start to hope too soon, only to have my hopes crushed.


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1 to “Is Hope Bad?”


  1. KTLFLA says:

    Of course you can be hopeful – just don’t over analyze. Go with it – stay optimistically guarded but don’t give up a chance at being happy just because you fear it may be doomed from the beginning. Have faith!


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