Someone in Chicago is shy and striking out on dating apps

An advice column where Chicago can ask questions on how to navigate life transitions, relationships, family, finance and more.

Dear Ismael,

It’s hard to find a good woman. I tried going on the dating apps, but everybody I meet is not who they say they are, and they always want you to send them money. I’m really not that good at talking to people face to face. I guess I’m a little shy.

— A Little Shy in Lincoln Square

Dear A Little Shy,

First off, don’t pay anyone to talk to them. Unless you’re into that — my respect to spicy content creators. But it seems a quick sexual high is not what you’re looking for in your search for the right woman.

You’re not alone in being shy. When it comes to dating, the universal question is: How do I approach someone I’m attracted to?

A memorable time when someone took a chance on me happened in college. I asked a classmate for a ride home, and he saw an opportunity to take me to an unexpected dinner.

He drove past my apartment, I let him know of his mistake, and he said, “We are going to dinner.” HOT! It was simple but worked better than the passive and tired, “We should hang out sometime.”

Everyone has different preferences. To help you see into a woman’s mind, I asked three of my close friends what worked for them. Not just from the first interaction but how the men followed through.

‘Persistent but not annoying’

This friend is independent, works hard and looks very sexy in a bikini. She’s a fire sign who listens to my pointless 40-minute stories and can make me laugh until I lose my breath.

“He kept being persistent but not too annoying or clingy,” she said of her fiancé. “He was really nice to me, and I never got the feeling he just wanted to sleep with me. He always sent good-morning texts.”

‘Genuine interest’

This friend is sweet, cute and very caring. She’s the kind of girl guys love to take care of. When her husband is driving and has to suddenly hit the brakes, he puts his arm in front of her so she won’t get hurt. I love it.

“I ended up messaging him [first] on social media without knowing anything about him except that we went to the same school,” she said. “What made my husband different was that he was genuinely interested in what I had to say. We bonded over our favorite TV shows. And the next day he’d ask if I caught the new episode. He never made it feel like a chore to text him, and we’d talk all evening.”

‘Helped me find love in myself’

This friend is creative and has that indie-girl vibe guys fantasize about. We tease her for the time a guy professed his love to her while she was minding her business at Walmart.

“What attracted me the most when I first met my husband was his confidence,” she said. “Maybe because it was something I lacked, but I loved watching him talk to our friends and tell stories. It was like watching a stand-up comedian. We had a lot of the same interests. And our passion for movies has become our love language. He became someone I can be myself around and laugh with. Because of that, it gave me more confidence and definitely helped me become more of a social person. He helped me find love in myself.”

Write to Someone in Chicago at someoneinchicago@suntimes.com.