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Hey Evan,
Your advice is great and seems to pertain to guys you’re already dating. I’m in a different situation. I’m interested in dating a male friend.
We met in college but were never really close and reconnected a year ago purely as friends. We started hanging out a lot the past year. He used to live two hours away so he would drive from far away to see me. I thought nothing of it. Then he moved to my city and we were close to each other now. One night we went out and he made a move on me. I froze. This was three months ago. We kept hanging out then, pretending nothing had happened, me sending mixed signals, both of us casually dating other people.
But I recently broke off casual dating because I realized I had strong feelings for him but now I wonder if it is too late? I still spend a lot of time with him and I don’t want to emasculate him by not letting him make the first move. We recently got back to a great momentum where it isn’t weird after all the mixed signals and I feel like I am ready to tell him I wasn’t rejecting him when he initially made a move on me but was just scared and surprised.
So should I make a move or will that emasculate him? And if we do date, do the same rules apply? Should I wait to sleep with him? Because I feel like we already have been on 100 dates (platonically), I don’t feel weird about sleeping with him sooner than I would wait for a guy I really like.
Help please.
—Jeannie
If you want to know what a man’s thinking, ASK HIM. Don’t ask your friends, don’t ask your dating coach, ask your boyfriend.
Dear Jeannie,
I was hoping someone would ask this question.
Because it gives me a chance to bring something up that I see all the time as a dating coach, especially in my private member forum. In that group, hundreds of women share their dating stories and support each other. And most of their questions sound just like what you wrote to me.
“I don’t know what this guy is thinking. I don’t know what to do. I don’t know what to say. What do you guys think I should say?”
This happens so often that I created an acronym to substitute for my full answer, so that I don’t have to write the same thing repeatedly.
OT
It stands for “overthinking”. Almost any time I get a “what is he thinking?” query, I’ll bust out my OT as a reminder of two of these two core dating principles:
1) Men do what they want. So if a guy is your boyfriend, he says he loves you, he calls you nearly every day, and then one time, he texts you, “Not now. I don’t feel like talking,” it doesn’t mean that he suddenly fell out of love with you, met someone else, and is planning on dumping you the next time you speak. It just means, “Not now. I don’t feel like talking.”
2) If you want to know what a man’s thinking, ASK HIM. Don’t ask your friends, don’t ask your dating coach; ask your boyfriend.
The reason that women choose not to ask their boyfriends what they’re thinking, even though their boyfriends are actually the only people who KNOW what they’re thinking?
The act of asking the question isn’t going to change the outcome — all it’s going to do is reveal what he’s thinking.
Well, there are two answers to that as well — the one you tell yourself and the one that’s really true.
The one you tell yourself is this: “I don’t want to upset him/emasculate him/bother him.” There’s some basis in truth for this, especially if you are perpetually acting weak, needy and fearful with a man who is doing his best to please you. The more you criticize and second-guess the intentions of a GOOD boyfriend, the more likely he is to get frustrated that you’re so insecure.
But the real reason you don’t ask him what he thinks is this: you don’t want to hear the real answer. You’re afraid of the truth. That he might be sick of your fears and insecurities. That he might need space. That he might be tired of the incessant conversations about where this is going, because he doesn’t know where this is going.
As always, I’ve hijacked the original question to make a point, and I apologize. But it’s important to know that your question is NOT going to change his mind on anything. His mind is already made up. If he’s happy with you, he’s happy with you. If he’s annoyed with you, he’s annoyed with you. And if he’s attracted to you, Jeannie, he’s attracted to you. The act of asking the question isn’t going to change the outcome — all it’s going to do is reveal what he’s thinking.
The only thing up in the air is whether you really want to know.
So instead of asking a dating coach on a blog who doesn’t know you or your friend what he’s thinking, how about you tell him EXACTLY what you told me? You were afraid when he made his move, now you’re falling for him, and you’d like to give things a shot.
If he’s not interested, he’ll let you know.
If he’s interested, he’ll let you know.
And either way, you’ll be able to move forward appropriately without all of this worrying and overthinking.
(By the way, he’s interested. I’m very happy for you!)
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