Can These Dating Tips Help Men Make a Good First Impression?

Ladies, I always enjoy reading your feedback and comments – and after 30 years, I still learn from all of you! Considering about 35-40% of my clients are men in the 50–80-year-old age group, believe me, after a recent divorce or being widowed, they definitely need help from the opposite sex on what resonates with you.

So, here are my thoughts – and at the end, I’d love to hear from you if I may have missed any!

1. Choose High-Quality Photos That Show the Real You

Don’t post one or two photos – post at least five. And they must be from the last two years. So, no photos from 10 years ago or your high school yearbook shot!

• A clear headshot with a genuine smile is a must.
• Include a full-body shot with natural lighting.
• Show off your hobbies with an action shot – whether you’re hiking, playing sports, or doing something else that defines you. We don’t care about your LinkedIn photo!

2. Write a Bio That’s Authentic and Captivating

Ok, wait a minute – maybe we should just say WRITE A BIO! Why do so many men skip that section? We want to hear your voice, your tone – it doesn’t need to be 10 paragraphs but at least one would be nice.

Your bio is your chance to introduce yourself beyond photos, so make it count. Keep it real, fun, and to the point – and skip generic lines like “I love to travel” or “I’m a foodie,” and share something unique about yourself.

• Highlight a quirky hobby or fun fact.
• Keep it short but intriguing… or ask us a question! As in “Where would you like to travel to next?” That can be engaging!
• Add a touch of humor if that’s your style.

3. Start Conversations with Confidence

Your first message can make or break your chances of getting a reply, so start strong. We can tell if it’s a copy/paste! And, always start by using our name.

Skip the “Hey” or “What’s up?” and take a moment to reference something specific from our profile to show you’re genuinely interested.

• If we love hiking, ask about our favorite trails.
• If we mention a pet, ask about its name, breed or personality.
• If we are into movies or music, ask for recommendations.

Confidence paired with a personal touch will show you’re serious about getting to know us.

4. Understand What Works for Women

Many online dating tips for women emphasize honesty, clear intentions, and great communication – and guess what? These principles work for men too.

So, please don’t lie about your age or height. Whether you are 71 and 5”6’ or 67 and 6”2’, we appreciate your honesty. And we are promising not to do the same!

• Be upfront about what you’re looking for but be respectful.
• Don’t send a message, then another, then another – it looks desperate – and give us a chance to respond. So, no double or triple texting.

5. Keep the Conversation Flowing (And Balanced)

A good conversation is a two-way street, so don’t dominate the chat or stay silent. Ask open-ended questions, share bits about yourself, and match our energy to keep things flowing.

After two messages back and forth each, ask us to lunch or coffee with a specific date and place in mind – it is so appreciated! When we do the same with you, please answer us back with a “great” or “your seem great, but I don’t think we are a match.” Be upfront and don’t leave us hanging!

Share a personal story or experience to deepen the conversation.

6. Skip the Cheesy Pickup Lines

You wouldn’t believe how many of these we get! Most pickup lines are a turnoff. Instead of relying on cliches, offer genuine compliments and focus on shared interests.

• Comment on something in our profile that caught your attention.
• Keep it light but engaging.
• Express genuine curiosity about who we are.

7. Be Patient

If we don’t respond quickly, know it may not be you. We may be on vacation or have a family issue going on.

Respect our pace and don’t rush the interaction.

8. Plan the First Date Thoughtfully

A well-thought-out first date will help set a positive tone for the rest of our relationship.

9. Be Positive and Self-Assured

Confidence is key, but it’s important to strike a balance between self-assurance and humility.

Be confident without coming off as arrogant. What can come off as arrogant to us is a list of “must-haves” – we are not talking 2 or 3 – but over that is quite a bit!

10. Keep Improving Through Experience

Not every match will turn into a relationship, and that’s okay. Learn from each interaction and refine your approach over time.

• Pay attention to what works (and what doesn’t).
• Get feedback from trusted friends or a good dating coach.
• Page 401 of my new book: 2nd Acts: Winning Strategies for Dating offers a simple log you can use to keep track of your online encounters! You may think you are messaging many people – but this way you have accountability. Each time you are online, send 5 thoughtful new messages.

And remember: online dating is a fast-paced game, so don’t overthink your messages. If you’ve got a great line or question in mind, go for it – waiting too long might cause you to miss out on a great woman!

Reader Questions:

Tell me ladies – what else should men know? Which tip do you think most men have a tendency to skip?