Dating shy older man

In fact, I always seem to have a good time when you're around! I would love to buy you dinner and get to know you in a more-than-friends kind of way, if you're up for that! For all you know, he's thinking the exact same thing you are. In fact, I think it's most likely the case. And if that's true it would be a tragedy if no one made a move. If you don't make a move, you'll always have regrets.


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If it doesn't work out, it sounds as if your friendship is strong enough to survive. Some times you have to take risks. It's time-honored, me-tested, successfully deployed: You are together, somewhere sunny. You are off, away from the group, talking, laughing. He says something personal, amusing. You look up from under your lashes, pause, and say, "Are you flirting with me?

There's something beautiful about this and your ask here. No writing, that would really puzzle him at first - although he might figure it out and 'get it' - it will puzzle him and consume too much brain power until he does.

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If his birthday or some other rare occasion that could include a card comes up, you could write a short note in it, and nothing very long. There are advantages too. By the way, Spring Fever is supposed to start things going like this. As above, YES follow your gut! So what if you're not? I have been that way, but that doesn't mean every shy person is. Try thinking of something you know you both love to do. If it goes well, then try to push it forward. This happened to me once, I was 24 and she was 30, and it lead to a relationship that I will always cherish.

If it works out, maybe show him how you'd like to be responded to and see if he's teachable.

Issues that are unique to shy women

Questions about kids, social group, future, blah blah blah don't matter at all if he doesn't return your feelings. So don't get hung up on this stuff; those are bridges you can cross if and when you come to them. You don't have to know the entire future and calculate every outcome to decide whether to speak about your feelings.


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With the benefit of hindsight in life, I say just go ahead and do it. It may meet your hopes, it may not, but you really have nothing here to lose. You can figure out the rest as it comes. Hand holding a problem? Lean up against him, side-to-side.

7 Tips for Dating a Shy Guy

Maybe just a bit ventral versus dorsal , so that it'd be natural for him to put his arm around you. Are you shorter than he is? Slide up his body. It can be done super subtly, but crap, is it ever so sexy. Check his body language; tightening up?

How to Approach a Love Shy Male?

Don't worry if he doesn't. You say that he's shy, be a bit aggressive and possessive. Keep the body contact up and maybe place his hands on you for him. That kind of behaviour isn't going to offend the vast majority of men; social inconveniences tend to only be significant if he is 1 really not into you, 2 you end up being really not into him.

And 1 isn't a problem once you get over him and 2 Only if he turns out to be totally clingy, which doesn't fit the profile. The potential positives outweigh the potential negatives. About the only thing I've ever learned in life is that nothing worth having comes without some sort of risk and sacrifice.

I can't tell you what specifically to do, but know this going in. Golden Eagle - "3 In my opinion, ask him to do something with you alone, but not as a date, or leave that up in the air. Most of the time I ask a group if they want to do X and on several occasions he's the only one to say yes. So the end result is doing X alone and then hanging post-X for a good chunk of time. My gut tells me I've kind of done this step - hence my back-and-forth about escalating Eternity, not Eagle, apologies Golden Eternity.

When you ask the group, he always says yes, no matter about others in the group, because he wants to spend time with you.


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Asking the group doesn't quite count for moving it up a step, because you had opened it to the group. I recommend you send very, very obvious indicators of interest--hair flipping, blushing, licking your lips, hardcore flirting, lots of smiling, open body language, bedroom eyes--until HE makes a move on you. I firmly believe that a lot of the anxiety in relationships is eliminated when the guy is the pursuer.

I wouldn't pursue this until you resolve the resentment you feel at always being the initiator, because there's a very real possibility that's what you'd be signing up for. I guess it depends whose perspective you are looking at it from. I'm a guy, and I have found that my level of anxiety in the early stages of a relationship is significantly reduced when the girl is the initial pursuer. So, I mean, if the OP wants to put the guy at ease Maybe your tight-knit group of friends already sees the obvious attraction between you both that is, if it exists, which it seems like it does and always backs out when this happens so that you two can spend time together?

Another problem with shyness is that shy people are often misinterpreted as being aloof or unfriendly. A guy may become even more shy if he is turned down repeatedly by someone he likes. Remember the old saying, "Once burned, twice shy. Worse, shy people, because of their unassertive manner, are often treated badly. People often feel at liberty to be rude to a shy person and say things that they wouldn't say to the extrovert. Studying a good course on shyness can help you understand how shy men act around women they like.

It's true that the symptoms of shyness can be hard to distinguish from sheer unfriendliness, but the best advice is not to worry about it. Try to make conversation with someone you think may be shy. Remember that you may have to do more of the talking with someone who is shy.

If you have a bit of shyness yourself, it will be harder to talk to someone who is quieter than usual. Ask questions of the shy guy to draw him out. Try to overcome any shyness you may feel yourself, and remember that you will have to put forth more effort to talk to a shy person. If you have too much trouble talking to the shy person, perhaps you need a little assistance in overcoming shyness yourself.

Anna Nicole Smith was onto something... 🤔

After you have had a friendly conversation with the shy person, repeat the process the next chance you get. Anyway any opinions are greatly appreciated, thanks! Share Share this post on Digg Del. Heck, he might be a bit stand-offish because he's thinking, "She's 15 years younger then me, she couldn't possibly be attracted. I would also say that this is likely. I know if some 20 year old acted like she had the hots for me, I'd constantly be asking myself, "Why in the hell would a young hot girl like her have the hots for me?

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