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Terribly shy and afraid of the letdown


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Ok so I'm slowly starting to attempt to get back into the dating scene. I like a friend of mine that I've know for a good while. I want to ask him out but I'm so afraid of making it awkward or being let down, but also trying to get out of my comfort zone and base it on if I never ask I'll never know...

(If it matters I'm 33 lol and still completely blind to cues from the opposite sex unfortunately. I have been known to misread signals...)

Any advise would be greatly appreciated.

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He's in my circle of friends. We talk every time he comes out. Thankfully it seems another friend kind of broke the ice me lol. I'll just have to see how it goes. He thought I was married to my ex so i was basically in the friend zone and he said he'd have to process the new found information. But we just recently had an hour long conversation in the phone while he was on the way to national guard drill

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Go in cautiously and start as friends. See where this leads you. Get to know him, enjoy good conversations, observe his personality and character. Over time, you will make the decision whether or not you wish to continue associating with him. Let time and listening to your gut and intuition be your guide.

 

Whenever I feel shy around anyone, I ALWAYS revolve conversations around the other person because people love nothing more than to talk about themselves, what they do, where they've been, what their interests are and the like. Ask away! Take great interest in the other party and any shyness and fear will be deflected. You ought to try this strategy.

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Do not blow a friendship on experimenting. Let friends stay friends and learn to get out and meet men otherwise. Ok restart your life by getting out more. Take some classes, courses, volunteer. Join some clubs and groups.

 

Get in shape, new clothes, update your look, etc.. Get on some quality dating apps with a good profile and fresh good pics and start talking to and meeting men for a low key coffee.

 

Don't lose friends by putting them in untenable awkward situations. It's not fair to him.

I'm slowly starting to attempt to get back into the dating scene. I like a friend of mine that I've know for a good while. I want to ask him out.
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Social skills are learned. You are not born with them. When you master them what you characterize as your shyness will disappear. You aren't so much shy as human. Like everybody else you fear getting hurt but part of love is risk.

 

Since you are friends & you do see each other, assuming you are not brave enough to ask him out, it becomes incumbent upon you to make it totally clear to him that if he got up the courage to ask you out, that you would say yes. Tease him about thinking you were married. Ask him how he feels about now knowing you are single & available or something like that.

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he said he'd have to process the new found information. But we just recently had an hour long conversation in the phone while he was on the way to national guard drill

Sounds like there could be something. I normally say go for it, ask him out it's a modern age, because I always has good results....but I'm a good at reading people, almost to the point I can see what they are thinking, while you have trouble with this which puts you at a disadvantage. So if I were you I would only lay hints, look pretty, and be very sunny/happy when we talked. Let him check you out/ start the chasing. I do understand you are excited about all this, and giddyup! you want results now! You have to set in a plan/strategy, and have patience. Let things happen organically, not forced. Have some mystery.

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Seems obvious to me that you're into him from his standpoint. Let him come to you. If he's lukewarm in his interactions in the next few days and weeks, take a hint. This guy isn't into you. When did your last relationship end? He thought you were married so you were probably living with your ex. Are you still living with your ex or separated/moved out?

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Seems obvious to me that you're into him from his standpoint. Let him come to you. If he's lukewarm in his interactions in the next few days and weeks, take a hint. This guy isn't into you. When did your last relationship end? He thought you were married so you were probably living with your ex. Are you still living with your ex or separated/moved out?

 

He's been pretty chatty the last couple of days. He told me if I don't have to work tomorrow I can come hang out with him and help him with a car he's going to be working on. And maybe I can get a better idea then of how it might go. I'm not going to be pushy at all. I do value our friendship and I won't be offended if he doesn't want to date me. But I'm trying to go out of my comfort zone and go by the saying you never know until you try lol

 

My last relationship officially ended a couple months ago. I was living with my ex until he took a job out of town in June. This guy does know my ex as do all of our mutual friends. But my ex also alienated everyone shortly after he took his new job..

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Ok. You may be lonely, but stay friends. If you come onto to him it will be awkward. At best it may be a hookup to scratch an itch or a fwb situation. However that he is friends with your very recent ex is particularly unseemly. Revenge sex happens but it rarely ends well. Why not date other guys and not this particular guy?

My last relationship officially ended a couple months ago.This guy does know my ex as do all of our mutual friends. But my ex also alienated everyone shortly after he took his new job..

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  • 8 months later...

Know yourself,Stop comparing yourself to others, Make friends with people who are more outgoing than you are,Be confident , Find people who share your interests , Go out more often, Improve your body language

Take first step. Finding that special someone is a challenge for everyone. This is true especially for shy guys who don’t know how to overcome the anxiety of going on a date with someone special.In contrary to the usually confident image of most guys, there are some who feel the opposite about themselves, and that’s why it’s difficult for them to communicate with other people, and it gets even worse if it’s about starting a relationship. Click here:

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