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Thread: Dating an older man - advice needed

  1. #1
    toughcookiegirl is offline Aspiring PUA
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    Question Dating an older man - advice needed

    Girl here. Dating advice needed about a guy.

    Met a guy at a social happy hour event a few months ago. I could tell he was into me, but didn't ask me out until I ran into him again a month or so later. I felt sparks and like we had something in common. I wasn't expecting him to ask me out (because he didn't before) but he did, and a week later, we went out to dinner. Super nice, thoughtful and gentlemanly. I couldn't tell, however, if he was into me, but he texted to make sure I got home OK. I wasn't expecting much after that, but a few days later, he texted again to ask me out. But he said that he's much older than me (he's 44 and I am 30) and that it's OK if I say "no" but he just found me attractive and hadn't thought about the age difference initially. I agreed to go out with him and we ended up watching a movie and he walked me home. He was traveling for the next couple weeks and then I was away one weekend. Again, I wasn't expecting much, but after his travels, he asked me over to his place for dinner and movie (he also texted once while he was away).

    I knew we had stuff in common, but it wasn't until we were hanging out alone at his place - away from outside distractions - that I felt more of a spark. Again, he was super polite and gentlemanly. I could tell he likes me, but is maybe somewhat intimidated? He implied something about how intelligent I was and how he has to use more of his intelligence around me. He made dinner (I helped a bit). We watched the movie and then I stayed past a bit for tea and we just talked. The whole time, he tried NOTHING with me - no kiss, no touching, nothing. And that was OK with me because I kind of wanted to get to know him more before jumping into anything. He walked me out and helped me get a cab. We hugged and I thanked him for dinner and he said something about how next time he'll add another ingredient in the dinner. He texted me when I got home and I texted back, he texted and I texted saying good night. And since then I've heard nothing (this was 3 days ago). Previously, a few days or almost a week would go by without any contact from him, but like I said, I am starting to like him more now and would like him to stay in contact a bit more. I keep wondering if the age thing is bothering him (he commented on it once in passing at his place) or something else.

    Mostly, I want to know whether I am being too silly to think that after 3 dates and a few sparks, he should be in touch more often and not let a few days go past without even texting.

  2. #2
    HardRock is offline PUA Forums Respected Contributor
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    Default Re: Dating an older man - advice needed

    There's nothing wrong with thinking along the lines of this in a practical way sort of..

    intent may be shown as soon as...but the part about him just not kissing at least got me thinking he might like you but may be taking low risks and settling for the current state when he may be adventurous and push for more in this dynamic.maybe yh or maybe no but yeah

    Mostly, I want to know whether I am being too silly to think that after 3 dates and a few sparks, he should be in touch more often and not let a few days go past without even texting.
    A girl once told me i will see. i wondered why and i noticed i stopped calling her because i was busy.so i phoned her and deep into the interaction she told me she would love to hear me everyday.Its not bad at all.

  3. #3
    Bballking is offline PUA Forums Respected Contributor
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    Default Re: Dating an older man - advice needed

    Take a step, help the guy out. If he mentioned his age being a bit of a factor, he may feel a little insecure about it. And if he hasn't tried anything, it most likely means, as you said, he is a gentleman. It sounds as if he wants to fully make sure that your okay with the age gap. The biggest thing you can probably do to show that, is not bring it up. If he brings it up, don't comfort him, don't listen intently, and don't try to sympathize, push past it. "I still feel like I'm way to old for you" You: "Haha, it's just a number. How did you get to be such a gentleman "

    If you reinforce it in any such way, he may believe your not okay with it, and it'll stick in the back of his mind.

    Again, for you text thing, help him out if you must. 3 days doesn't seem to be a large time line for your weekly dating scheme, but if you feel it's been too long throw him a text to show a little interest. This will give you a better gauge and help you understand your stance in your relationship. Ex: "Hi there handsome" Man up sista

  4. #4
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    Default Re: Dating an older man - advice needed

    i'm going to say that he is definitely "playing it safe", either he really doesn't want to mess this up, or he thinks you don't like him as much as you do.

    try showing more sexual interest, that should make him more confident about taking things to the next level. (I know that if a girl is showing tons of sexual interest in me it makes me feel a lot better about taking risks and escalating) you can do this by playfully touching him, and even telling him what you like most about him. (I do this to girls and it drives them insane if they're attracted to me) if he reciprocates the interest then its on

    btw, he may just be a really shy guy, or he might have just gotten past a divorce or bad breakup.

    also, its ok for you to text him when you feel like it, I love it when girls randomly text me. it gives me an unexpected pleasantry and often makes my day (especially if they have something interesting to say besides the typical " what's up?")

    good luck, I hope things work out for you

  5. #5
    Rookie22 is offline Aspiring PUA
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    Default Re: Dating an older man - advice needed

    usually age won't matter if the convos you guys have flow and certain topics aren't off limits due to lack of knowledge. Based on his actions he's a passive person, and I'd say he's unsure of how attracted your are to him, because it seems like he's waiting on a strong enough hint of your interest before making a move.

    As for him not staying in contact enough, I would use convo clues such as his work schedule, dating status, lifestyle etc... to connect those dots. So are you being silly? No, you just gotta give stronger hints.

  6. #6
    toughcookiegirl is offline Aspiring PUA
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    Default Re: Dating an older man - advice needed

    Thanks to everyone who responded. Still haven't heard from him.

    He brought up the age thing once when we hung out - we were watching a movie where a much older man was dating a younger girl and he said something about how this is a bad movie for us to watch. I don't know if that was a joke or just said thoughtlessly or it's something that bothers him, but at least I know he doesn't think of me as just a friend.

    I think at that point, I may have laughed a little and playfully hit his arm (very lightly). He definitely noticed that, but didn't respond to it. I figured that maybe he does in fact want to take things slowly. Aside from the goodnight hug, that was the most physical contact we had.

    One thing I was wondering about was - his bedroom door was open and I could see a neatly made bed. Did he clean / make the bed just for me? I mean, I do that when people come over...but, he'd also left the door open (which I am not sure I'd do).

    I have no clue about his romantic past. I did wonder if he's been divorced or really hurt in the past. At one point during the movie (there was a cheating couple), he said something about how he doesn't understand how someone can live a duplicate life like that. He said that once his friend was tempted to cheat on his wife, but didn't. And I said "I don't know, but I also have a friend - not someone I am close to - who is having an affair with a married guy."

    But, I can't make assumptions about it, and while I can be understanding, I cannot and will not attempt to coddle him if he's incapable of being in a relationship because he hasn't gotten over his past.

    How do I know if he's playing it safe or just not interested anymore?

  7. #7
    meteora's Avatar
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    Default Re: Dating an older man - advice needed

    How do I know if he's playing it safe or just not interested anymore?
    he's playing it safe, if he wasn't interested he wouldn't have even bothered to tidy his place up.

    i'm going to go out on a limb and say that he has been hurt severely by some woman who cheated on him (based on what he said about people living double lives)

    i'm going to say that he's probably playing it safe because he's looking for a girl to settle down with. he's definitely not a player. he wants to know that you like him and him only. keep spending time with him and giving him little hints that you care about him.

    too often girls confuse a guys insecurities for dis-interest. truth be told a lot of guys have the same kind of confidence issues that you girls go through.

    the more interest you show the more interest he should show. simple as that, if he's dis-interested in you and not just dealing with his confidence, he would send some solid IOD's your way.

  8. #8
    Lazarus is offline Aspiring PUA
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    Default Re: Dating an older man - advice needed

    It's so refreshing to occasionally get a female view on this whole "dating" thing. And to remind us you're not just a piece in "the game" but someone with their own issues and insecurities.

    I would say (like so many others have) that he's playing it safe. He sounds like a traditional, slightly old-fashioned guy to me. To a guy like that the age difference could be a very significant faux-pas. So, I would advise you to initiate contact (maybe a casual text message along the lines of "I had a good time with you"), and try to find a way at some point when you're interacting to somehow reassure him that you're fine with the age difference (it's up to you how direct or casual to be).

    And as far as him making his bed goes, he could just be a very neat person. Some guys are, so I wouldn't read to much into that.

  9. #9
    DirtyOnPurpose's Avatar
    DirtyOnPurpose is offline PUA Forums Respected Contributor
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    Default Re: Dating an older man - advice needed

    Aww, you've got yourself a keeper there ma'am!

    I'm not sure, but hopefully in two dates you'll get a kiss on the forehead. Good luck.

  10. #10
    easyflow is offline PUA Forums Respected Contributor
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    Default Re: Dating an older man - advice needed

    He is not interested. 3 dates and no kiss. He sounds like he might be gay, nothing wrong with that. I wouldn't contact him.

    You will know when a guy is into you. He will call/text, anting to meet up, wanting to eventually get intimate. Having his bed made and his door open, doesn't mean anything, I think your over thinking this.

    If you do see the guy again, and your at his house, start touching him while watching the movie, tell him you are cold, get a blanket and cuddle with the guy. Play with his hair, get some contact going on. Get your tits onto his body. Playfully. If he doesn't make a move, or gets upset, dudes not into you girl.

    Leave and delete number.


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