Dating question ... how should I proceed?

This is long. Sorry.

I'm a little embarrassed to ask this as a 45 y.o. female, but having not dated a ton I'm not sure what to do. One friend tells me to say what's on my mind, another find says "take the hint, he's not interested. He's too young anyway. He's going to want children, etc." Not long ago I met a guy that was super hot (and for my age, I hear I'm pretty sexy so its not like I'm an ugly duckling) but this guy is 36. I came across him on a dating site. We started chatting, emailing, then texting (no talk on the phone, though I could have called him but we were having such a great time laughing over email and text that I waited - and I guess I thought HE would eventually want to talk live.) I acted spontaneously one night about a week after we had started chatting and asked if he wanted to meet for a drink as I was already out at a bar (I had no intention of inviting him out but when he texted me out of the blue when I was having dinner with a friend that night, when he didn't know if I could have been on a date, and then during the course of the next few texts told me he was "at home" that night, I took a chance. I thought it would be more casual, less time to anxious.) While we had had a laughing "relationship" (a lot of joking around but still plenty of flirting) I wasn't expecting more jokes when I asked him to join me (nothing mean from him but not giving me an answer). I got upset (though I didn't say anything) but I didn't contact him for 4 days. I had hoped he'd contact me, perhaps wonder where I had gone. My friends told me that should be my first clue. Finally I contacted him (via email). I was once again casual and light. Didn't let him know I had been upset. He replied to the first email (where I was my usual joking self) but never replied when I sent him the next. In the days that followed, I wondered if I had been "too" light and casual or "too" joking. I thought maybe he took my reply to his email the wrong way (nothing mean, just joking as we had been doing all along). But I had truly thought that - since we had been teasing and ribbing each other from the start - he would see my reply as a joke. He knew me well enough to know I like joking. When I didn't hear back from him, I figured, "well, it never would have worked out anyway. He's way too young for you. He was probably just having fun." But we had SUCH a connection. It felt like the chemistry sizzled even over text. I am truly surprised he didn't contact me and that he was willing to walk away from what I thought we BOTH felt (and I think I'm a really good catch - even 9 years older). Two weeks has now passed and I have sort of been feeling like saying hello and asking him how the "search" is going but friends have told me to "take the hint" and that he's obviously "just not that into you or else he would have reached out." What I REALLY don't want is to look desperate or ridiculous.

So, any advice?



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What Guys Said 1

  • you are hiding your feelings and over-thinking his actions (or lack thereof). stop, calm down. you need to get over this little bump and contact him again. joking over text is an easy way to miscommunicate, and it sounds like that's all that happened. go ahead and resume contact like you described in your question, and try not to overthink things. he's not interested in creating drama, so he's not going to play mind games with you.

    do keep in mind, though, that a few men like the fantasy of the connection and will never manage to meet you in person, on purpose. if things continue to be awkward and you haven't met after a few weeks or a month, leave it. life is to precious to spend chasing the uncatchable.

    • Thank you for being so sweet and helpful. So you don't think I should "take the hint" as my friends say? Wouldn't he have contacted me if he was still interested? He hasn't even looked at my profile since this incident when he was looking at it every day prior to this. *Also* there is a BIG age difference (and he is SUPER attractive). My friends say he'll want kids and I can't imagine (no matter how "cute" I may be) that he'll want an "old lady."

    • Well, I took your advice. Made a fool out of myself. Guess I was right when I wondered about those 2 days I saw him online non-stop. I sent him a casual email. While he's was very nice in his reply, he wrote that he had "found someone". Stupid me.

    • don't beat yourself up. you took a chance and it didn't play out. that's unfortunate (he sounded like fun), but it's not the end of the world and you handled yourself elegantly. I wouldn't think the age difference is that big (I've seen bigger), but with kids on his mind, that does change things a bit. sorry I led you down a dead end road. keep your chin up, and good luck!

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