How to Learn to Flirt After 40 If You've Been Shy Your Whole Life

Practice it in small, low-stakes steps, the way you'd learn a language. Start by saying hello to people you have no interest in dating. Then ask real questions and pay attention to the answers. Then tell a woman you like, lightly, that you get a little shy. You don't need a new personality. You need repetitions.

Flirting is a set of habits: eye contact, a smile, a question, a light tease, and a clear invitation. Nothing below depends on you being younger.

A man in his 40s or 50s often has real advantages: less panic, more self-knowledge, more patience, and less need to perform. Calm reads as attractive when you're also showing real interest.

Shyness is usually a fear of getting it wrong. A C-VILLE Weekly column on flirting says the more you worry about the outcome ("I'm probably not her type"), the more you clam up with self-consciousness. Its advice is to stop putting pressure on each exchange and focus on getting practice, not on picking people up.

So change the goal. Each conversation has one job: get one more repetition.

Do each step with people you aren't trying to date first. Waiters, neighbors, coworkers, cashiers.

Weeks 1 and 2: Smile and say hello. Acknowledge people as you pass them and hold eye contact for a second. A flirting handout from a psychologist at the Feeling Good Institute calls this a first step in exposure for social anxiety, and says it signals you're open to interacting. Use a plain "Hi" or "Morning."

Weeks 3 and 4: Ask one real question. The same handout says to keep the spotlight on the other person with open-ended questions, because that reduces the pressure to be witty. Try:

• "What do you do when you're not working?"
• "What's the most random thing you've gotten obsessed with lately?"

Then listen, and follow up on one detail she gave you.

Weeks 5 and 6: Add one genuine compliment. The handout suggests simple things first, like an outfit or a smile. Say it once, plainly: "That's a great jacket." Then move on to the next topic. Don't wait for a reaction.

Weeks 7 and 8: Say the shy part out loud. Reid Mihalko, a sex and relationship educator, says you should tell people what's going on for you. His example is to say you like flirting with her, that you're getting shy, and that she might have to work a little harder. The handout suggests something similar: "I'm a really shy person. Sometimes I don't know the right thing to say or worry people will think I'm boring because I'm not talkative. Do you ever struggle with what to say when you are meeting new people?" That also gives her something to answer.

If you start a conversation with a stranger, the handout suggests giving yourself a time limit, such as "I just have a minute before I have to meet my friends, but I wanted to ask you...", which tells her you won't take much of her time and takes pressure off the approach. Then ask for her opinion on something in front of you: "Have you tried this? I'm trying to find something new."

If you lock up, you have options. The C-VILLE column says to breathe through the feeling instead of fighting it, and to look away for a second or two to reduce stimulation. It also suggests a joke: "Look at me, I'm all tongue tied."

Afterward, don't replay every detail. The same column warns that this invites your inner critic to tell you that you stuck your foot in your mouth.

Mihalko also suggests that when talking is hard, a text or a note is a legitimate way to flirt, and that a friend can help by telling you to take a breath.

You don't need lines. A flirting article on Sixty and Me, written by a dating coach for women over 50 flirting with men, lists simple moves that carry over: make real eye contact without staring, include her name in the conversation, give a casual compliment, and sit next to her instead of across the table so it's easier to lean in. It also suggests repeating back what she says in a light, teasing tone.

She says: "I went to the gym today." You say, lightly: "You went to the gym. Do tell."

Brief touch comes last, and only after she's clearly leaning in. The psychologist's handout says to start with body language like a smile and a slight lean, and to try touch, such as a brief arm touch, only if she responds positively.

If she gives short answers, avoids eye contact, or never asks you anything back, don't keep pushing like a salesman behind on his quota. Step back.

If she's engaged, laughs easily, and leans in, be clear and say what you want.

• "I like talking to you. We should grab a drink this week."
• "You're trouble. I'm keeping an eye on you."

Light and clear beats vague and needy.

The handout suggests ending a conversation before it gets boring or tedious, so she leaves wanting more. It also shows you aren't desperate for her attention. "I have to get going, but I'd like to keep talking. What's your number?"

"I'm too old" and "I've always been shy" are both reasons to stay home. Neither is a reason to avoid saying hello to one person this week.

Pick tomorrow's repetition now. One hello, one question, one compliment. Then do it again the day after.