One way you can develop your own sense of style is to find an older style icon and emulate their style. This could be a classic film star like Carey Grant or Grace Kelly, or it could be your mother or father’s style in the 70s or 80s. Look at how your style icon dresses and carries themselves. Try to find clothing that has a similar cut or look and style yourself after an older style icon. If you’re trying to create an outfit for a night out, you should think about dressing mature and still true to yourself. This could mean higher necklines and lower hemlines, but also an element that is true to your personality or sense of style, like a cool necklace or a vintage coat. The idea is to project confidence and maturity with how you wear your clothing, rather than what you are wearing.

You can become well-versed in current events and pop culture by reading articles online and in print in magazines, newspapers, and journals. You can also watch videos online about pop culture and world issues so you are armed with lots of intelligent information you can discuss with the older guy.

One way you can show off your skills or abilities is to invite him to an event or setting that will allow you to demonstrate them. This could be an art show displaying your artwork, a sporting event where he can watch you play, or an office event where you can show off how well-regarded you are among your co-workers. You can also share this information in conversation by asking the older guy what he is most proud of or asking him about his skills and abilities. He may then reciprocate by asking you about your skills and abilities, thereby allowing you to share them without appearing cocky or egotistical. For example, you could suggest: “Let’s talk about things we are proud of” or ask him, “What do you feel you are good at?”

You can also plan dates or get togethers that focus on a topic or activity of interest, like going to see a favorite author read at a bookstore or going to watch a hockey game of a team you both love. This will show the older guy that you are trying to create experiences that you will both enjoy and that you are mature enough to consider his needs as well as yours.

Do active listening with the older guy by asking him about his day and then listening to him fully as he speaks. [9] X Expert Source Maria AvgitidisMatchmaker & Dating Expert Expert Interview. 20 December 2019. Listen without interrupting but show you are engaged by nodding and maintaining eye contact with him. [10] X Expert Source LeTisha UnderwoodCertified Professional Matchmaker Expert Interview. 14 December 2021. Once he is finished speaking, repeat back what he said in your own words, such as, “I think you mean…” or “What I hear you saying is…” You can also offer advice or comment on what he tells you. Be thoughtful and take your time when you respond to him, as this will show him you take his words seriously and can be a good active listener.

Keeping your feelings and emotions to yourself may seem like an easy to avoid conflict and appear relaxed and easygoing, especially if you are trying to appear cool and collected to an older guy. But being dishonest about your feelings will only lead to conflict later on and less trust between you and the older guy. If the older guy is as mature as he seems, he will react to your honesty with compassion and gratitude. For example, if the older guy does something that upsets you, rather than get upset and start a screaming match or give him the silent treatment, you can respond by suggesting that you both discuss the issue and try to resolve it together. If he forgets your birthday, for example, you may tell him: “I’m sure you didn’t mean to be hurtful, but when you forgot my birthday I felt really hurt. It felt like you didn’t value a day that’s important to me. Can we talk about it?”

This means not calling or texting him all day, every day, or insisting that you spend every minute together. You should cultivate your own friend group and stay connected to your family and friends, even if you become involved with the older guy. This will illustrate your independence and likely lead to a healthier relationship. Do things on your own occasionally, like going to a concert or seeing a movie. Knowing that you can have fun by yourself will make you more confident, which is impressive to older guys.