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This is coming from someone who currently has dated, fell in love, and is marrying a shy guy. Sometimes they are shy and sweet, shy and nervous, or sometimes, just shy. How do you get them out of their shell?
Most guys approach a situation from a logical standpoint. If it makes sense then they will usually find a way to do it. While my man is very shy in large groups of people, he's found ways to get around his shyness at work and school. He converses well and is extremely smart.
What if you can't get your shy guy to open up a little bit? It all depends on timing.
If this is your first date with this shy man, don't let go of him too quickly. Give him a chance to get to know you. Unfortunately, a good number of men are shy or nervous about dating because they have been burned in the past. Don't assume why he is shy, but instead embrace his shyness and make him feel wanted and comfortable. Sometimes you will need to control the conversation and steer away from topics he may be sensitive to at first.
Go somewhere for dinner, offer a place where you're able to talk without too much of a crowd. More importantly, though, have fun! Be conscientious of your date and just have a good time. Your laugh might be infectious.
The Fifth or 10th Date
It will take a few or five dates to get him warmed up to you. The more times you go out and you are honest about yourself, the more he will open up. Don't say you like something if you don't, and don't agree just because he does.
Men don't like to go out with a woman thinking she's just what he's looking for, only to find out that you hate half the things you said you liked. You don't have to be perfect matches. We all know where that got Anna from Frozen: Sandwiches.
By now you will know each other better, so start giving a little bit of the control back and let him take the lead slowly. That doesn't mean, "Whatever you're up for" or "Whatever you want to do," it means if he suggests something that might be fun you say: "That sounds interesting, let's do it!" or "Sounds great!" Having a positive attitude is key.
If you're someone who struggles with negativity, this will be good practice about changing to positive thinking. There are not many things you should change about yourself, however, being a positive thinker can help you not just in dating, but also in life.
Shy Guy's Last Chance
At some point in your suggesting and his shying away there needs to be a time where you put your needs/wants forward. Ideally, this would have been a topic of discussion early on, but sometimes it needs reaffirming. Go to a nice dinner and talk about some of the things you like to do. Talk about what is important to you. If it's something he can "work towards," that is positive and a sign you might have a good guy. If he blows you off and decides this isn't for him, let him go peacefully and kindly.
A breakup is not an image of what a man does or does not want from you. It's not a personal list of things you need to change. Sometimes people just don't fit together well. Some men don't like to be pressured, some are confident, brave, and thrive under close conditions.
Treat others like you would like to be treated. There are some things we can live without in a relationship. Your first priority is to decide what you can and can't live without. What is most important to you? Outline this clearly so that the man you're going to date knows exactly what you want. That goes for men, too.
Listen to your date's words. Is he sincere, because if he is then it means he is genuinely trying to make small changes. It means he really likes you.
Never take advantage of a man or abuse his trust.
We ask this of men—well, men ask this of us, too. Be appreciative of your date/boyfriend. Show him you trust him and he will trust you. Give your date as many openings for improvement as possible.
Anything done in the bedroom should NOT be judged in his overall character. Better bedroom moves can be taught and improved, but a personality is worth a thousand words.
When men trust a woman, it's a very difficult thing to do. To give trust to anyone is hard for a man. Men are usually very loyal friends, they are strong companions, and usually defend what they like/love.
If your date defends you, stands up for you, or says he trusts you, do not take it lightly.
Is shy guy still shy?
If you get to around two or three months of solid dating, and your guy still isn't up for doing the things you like to do, then it's time to say goodbye. No one should force anyone to do something they don't like. Be courteous, sweet, and mutual with the breakup. It's not a victory. You're not getting rid of a pest or a pet who ruined your Gucci boots. This is a man with feelings and emotions.
"I really enjoyed spending time with you and you are a lot of fun. I just don't think we match up as possible partners."
"You're a great guy and I loved spending time with you. I just feel like we don't want the same things."
"I don't think we're meant to be. You deserve to find someone who will love all of you. There are things I want that you're not entirely open to, and that's okay. It just means we still need to find who we're supposed to be with."
Have a kind heart, but be honest. Even if your date is mean, says something hurtful, or is spiteful because of a breakup, continue to be kind. The hardest thing about being a good person is continuing to be kind, even in the face of hatred. You are better for being that way though. It's a positive image on you and a negative one on him.
Find your one and only, never let him go, and may you walk the road less traveled.