Should I ask him out?

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Should I ask him out?

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  • Hayley Matthews Hayley Matthews
    DatingAdvice.com
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    angi76
    angi76
    Participant
    March 4, 2018 at 10:56 am #166786
    Should I ask him out?

    I met a younger guy online who pursued me. It started out sexual but I couldn’t meet up at the time and we ended up texting and talking on the phone everyday for the next week until we met. He lives an hour away and is also new to the area so he wasn’t sure where to go but ended up suggesting a restaurant near his place. We’ve hooked up a couple times, a week apart on his days off, both times at his place. He has a roommate and no room of his own but I told him my place was off limits (I’m in the process of moving). The last time was two weeks ago and I initiated things so I don’t want to again. We’ve texted off and on and he’s nice and responsive when I reach out but he hasn’t mentioned getting together again. He has said multiple times he thought he bored me. He mentioned that he’s shy and I think he feels he has nothing to offer. I’m interested in getting to know him more, not just sex. Should I make the move and ask him if he wants to meet somewhere? (Like a real date)?

    gwes90
    gwes90
    Participant
    March 7, 2018 at 1:17 am #166952

    Yes, go ahead

    shutterbugbali
    shutterbugbali
    Participant
    March 7, 2018 at 6:26 am #166954

    Yes

    nancy_rowlet
    nancy_rowlet
    Participant
    April 6, 2018 at 9:40 am #169776

    I’ve dated a person younger than me- he was an explorer and it was embarrassing haha

    PRW
    PRW
    Participant
    April 6, 2018 at 2:05 pm #169832

    Nothing wrong with you pursuing him and asking him out. But keep in mind what you are getting into.

    We’ve texted off and on and he’s nice and responsive when I reach out but he hasn’t mentioned getting together again. He has said multiple times he thought he bored me. He mentioned that he’s shy and I think he feels he has nothing to offer.

    When people tell you what they are like,…believe them. This is a low confidence insecure guy. He doesn’t have his own place with even his own room,…what does that say? This is not a strong leader,…more like a puppy that will follow you home hoping to be taken in. Puppies are cute, but what are you going to do with a puppy? You can try to work with him and push him to be more confident, to make the plans (without your help), and to take the lead, but it will be an uphill battle.

    Your choice, but just keep in mind what you are signing up for.

    • This reply was modified 6 months, 1 week ago by PRW PRW.
    • This reply was modified 6 months, 1 week ago by PRW PRW.
    Robansas96
    Robansas96
    Participant
    April 7, 2018 at 8:03 pm #169881

    Why not? What could go wrong? Maybe that’ll be your best decision ever made!

    jamesdean
    jamesdean
    Participant
    May 17, 2018 at 4:07 am #174390

    yeap

    darenmartin
    darenmartin
    Participant
    May 17, 2018 at 9:39 am #174426

    As you mention in your post that you are doing chat, phone calls with each other since a long time then you should ask him for a date without any hesitation. Might be he is waiting for you to ask first.

    mimijanell
    mimijanell
    Participant
    May 20, 2018 at 10:50 pm #174664
    Reply To: Should I ask him out?

    stay strong and always follow your gut feeling.