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Dating : Re-Connected and clueless

Dating : Re-Connected and clueless


33/f here. Recently re-connected on Facebook with someone from my past, 35/m. He was my best friend’s stepbrother when I was in middle and high school and we spent a lot of time as kids together. Anyway. Past 2 days we’ve texted non-stop, last night we both admitted we liked each other years ago and have continued to wonder about each other, blah blah blah. We’re both single, I just recently ended something after a few months, and I’d really like to see him. He hasn’t asked me out or tried to make plans. Is it too forward for me to ask what he’s doing this weekend? Too soon? Wait until he makes a move?

What do you think?

2 Comments

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  1. In short I say ask him out. You will know by his response. Life is too short to wait around. If you are interested in him put it out there. Would you confess to having a crush on someone if you weren’t still open to it?

    27/f here. A few months ago I was in a similar situation! I bumped into someone that I had known well growing up. The same basic thing happened texting non stop and seemed to have a lot in common. He didn’t ask me out and I was beginning to wonder if he was not really into to me. Then I just took a leap! We had a great few dates and good chemistry but didn’t want the same things in the long run.

    All this to say I would still just be sitting here crushing on him if I didn’t at least try!

    RISK IT TO GET THE BISCUIT!

  2. >Anyway. Past 2 days we’ve texted non-stop,

    That is never good. That is at least a day and a half too long without the guy offering a date. Shows gutlessness on his part.

    >last night we both admitted we liked each other years ago and have continued to wonder about each other, blah blah blah.

    More indecision and dancing around the bush.

    >He hasn’t asked me out or tried to make plans.

    That is the root of the problem.

    >Is it too forward for me to ask what he’s doing this weekend? Too soon? Wait until he makes a move?

    You could, but then how long are you going to put up with the timidity and lack of confidence that should have been there in the first place? You’ll probably eventually loose respect for him and any feelings you have would evaporate.

    You would be much better off to say something to him like, « *Are we going to dance around the bush for weeks, or are you going to make a date?* ». And then expect him to wake up and make a date. So even though you had to make some kind of a move first, you also made it clear that he is the one that needs to take action and you did it in a way to « jar » him out of his « daze ». But if he stutters and stammers around, pees down his leg, and can’t bring himself to make plans without you helping him with every detail,…then you need to move on. He is 35yo, not 15.

    But if he doesn’t want to make a date than he is just not as into you as he said,…and move on.

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