I am 45 and nothing has changed from when I first started asking girls out. Since I was a teen, I’ve always been kind of shy, but at least have the courage to ask some girls out that I was attracted to. I always, throughout my life, would get a girl to meet me for a date, and then she would never respond to my calls ever again, and like clockwork, that seems to be the same old story. Although now, I can’t even get a girl to go out with me. It seems as if once I like a girl she automatically doesn’t like me. I meet girls and we connect on social media and maybe get each other’s phone numbers and once I start showing interest, they will never talk to me again. In fact, you can even see them avoiding me. I’ve become good at detecting that so I just don’t understand what it is that I am doing as I am a gentleman as I was told I am not one who is looking for sex, right away, at least. So I just don’t understand I’ve never had a girlfriend. And when am I going to finally find that girl? I try to meet girls in mutual interests, like church, like theater, like martial arts. These are all things that I am interested in and I am involved in. But it doesn’t matter. Once a girl meets me, she likes me, once I show interest, even if I didn’t ask her out, she will never speak to me again any insight?
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I'll list some stuff here and whatever seems most relatable to you, I would encourage you to do some online research about that topic, find a workshop or videos on relationships, or simply just ask people in your life for help (family, friends, coworkers, etc.). Find someone who can join/watch you interact with women and ask for honest feedback. Don't be afraid of criticism, use it as a tool to help you improve yourself.
The first thing is that you're not confident. Even if a person is toxic or ugly as a troll, if they're confident they will have people chasing them. Also being able to make people laugh is a HUGE deal. Try to find some really good or super corny lines and practice them in front of a mirror and on random people. The more practice you have, the more confident you'll become.
The second usually comes down to HOW you're saying things or treating people. If you suck at flirting then you come off as super creepy and girls WILL avoid you. If you're saying offensive things, objectifying them, getting angry/starting petty arguments because you feel rejected or disagree with them, they will avoid you.
Thirdly, conversational skills. If you're boring, there's nothing to become interested in. Talk about what you're passionate about, your goals, your deepest desires, get creative with it. Don't ever trauma dump. If you immediately tell them your whole life story or super personal details such as never having a serious relationship, being a virgin, being super depressed/lonely, past traumas, whatever. That comes off as super cringe. On the flip side of the coin, it could be that you're talking too much about yourself without asking about them or letting them speak. No one likes having a one sided conversation. Everyone likes to feel heard and everyone likes to connect with people on a personal level. So try to balance the conversation so both of you spend an equal amount of time talking about each other. Ask questions.
The fourth reason usually comes down to self care. Get a hair cut, shave or trim facial hair, wear extra deodorant, spray a little cologne, wear clothes that fit your body and look good on you. A person who doesn't care about their appearance typically comes off as unattractive. If they aren't taking care of themselves or their own needs, how could they possibly care for another person's needs?
Lastly, are you going after women your own age or women significantly younger? Most younger women do not want anything to do with older men. What do you have to offer in the relationship? Are you more of a caregiver where you will take care of their needs financially/emotionally? Are you more of a protector where you will make them feel safe? Are you more of a lover where you will take care of their every need romantically?
Gotta looks hard at yourself. Really delve into what you did or said and take all the advice, feedback, criticism that you can. Don't get angry at the people telling you the truth. Use that to your advantage and change your approach. Hope this was helpful. Good luck.
Your shyness probably has a lot to do with it.
Shy doesn't work very well.