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Dating in Pittsburgh? Here are 5 Proven Dating Tips for the Modern Gentleman

June 2, 2022

For many singles dating in Pittsburgh, first dates are intimidating. Your date will form her first impressions of you and get to know you more to determine whether or not she wants to pursue a second date with you. You hope that your first date goes well enough to lead to a second date. That’s why today we will be breaking down 5 of our proven dating tips for the modern gentleman to help you show your confidence and secure a second date. Let’s get started!

Tip 1: Dress to Impress

Put your best foot forward for your first date in Pittsburgh by carefully selecting your outfit 

Woman touching man's bow tie at a table

When dating in Pittsburgh, your style will be one of the first things your date notices about you. How you dress on your first date shows a level of self-respect and sets you apart from the crowd. What you wear on your date will be determined by the venue, so when selecting your outfit, choose wardrobe capsules to wear on different types of dates. For an evening out on the town in Pittsburgh, a dark tailored suit or tux is an essential piece to have in your wardrobe. For a venue that is a bit more casual, a well-tailored pair of jeans and a well-fitted shirt will show your date the effort you put into your appearance. Overall, it’s best to wear something that makes you feel confident yet comfortable. A woman appreciates a gentleman with class. If you treat a woman with respect and look great while doing so, your efforts will prove to be successful. 

Tip 2: Show Your Confidence

Be the most confident version of yourself on your first date in Pittsburgh

Man and woman sitting on a boat

Your wardrobe will set the first impression for your date, but your confidence will determine how well the date goes. Women want a real man who is comfortable in his own skin, so show your confidence. Don’t try to be something you’re not—it never works out! If you show your date a false version of yourself, she will know down the line that you have not been honest about who you really are. Your date wants to get to know the true version of you, so be your most authentic self on your first date in Pittsburgh.

Tip 3: Flirt With Class

Use tension-building flirtation to impress her when dating in Pittsburgh

Man and woman dancing

Don’t be afraid to flirt on your first date—but do so tastefully. Be bold but respectful. Do not use cheap, insincere pick-up lines or sweet talk. Instead, compliment your date. Comment on her outfit or what you like about her personality—just make sure your compliments are not only centered around her appearance. Tension-building flirtation is a clever technique to use on your first date in Pittsburgh. Mix compliments with humor to tease your date in a flirtatious way but don’t insult her. Women love a great sense of humor. Smile and maintain strong eye contact during your date so she knows you are giving her your full attention. 

Tip 4: Keep the Conversation Positive and Light

Conversation is key when dating in Pittsburgh, so think of topics to keep the conversation going

Woman laying head on man's shoulder at a dinner table

The conversation during your date can make or break the experience. Keep the conversation light. Do not turn your first date into a job interview or an audition for marriage. Encourage your date to talk about herself. After all, it’s not all about you! Think of some easy conversation starters before you go on your date, and ask her questions about herself. Your date wants to know more about you, too, so make sure you contribute to the conversation. Remember that silence is golden—a few moments of silence during your date are welcome. 

Go into the first date with a positive outlook. Don’t let previous bad dates or romantic experiences hinder your future experiences—look at each date as a new beginning! Keep details about your ex-spouse or prior relationships out of the conversation. Avoid discussing politics, sex, or religion on a first date. These topics are insulting, and she won’t want a second date if this is all you talk about. 

Tip 5: Chivalry Is Still Alive

Show your date in Pittsburgh that chivalry isn’t dead

Man smiling while holding a fork up to woman's mouth

There’s no denying that women think chivalry is romantic. When you get to the restaurant, hold the door open for her. Let her have the window seat. Don’t look at your phone during the date unless it is an emergency. It is disrespectful, and this behavior will never lead to a second date. Remember that desserts can be sensuous, so insist that she has the last bite before you end the evening. When the date is over, walk her to her car. After the date, call or text her to make sure she gets home safely. 

First dates can be intimidating, but with these 5 proven dating tips, you will have all the confidence you need to sweep your date off her feet. At The Modern Matchmaker, we understand the challenges of dating in Pittsburgh. We offer matchmaking services for men to help navigate the dating scene to help find their perfect match. If you are interested in matchmaking services, contact The Modern Matchmaker today to understand how our expert team of matchmakers can help you.

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