A Perfect Gentleman's Guide to Dating

I recently spent several months watching a socially awkward acquaintance of mine, who's in his mid-50s, make mistake after mistake in his quest for a long term relationship with a woman. Every time he made a mistake, I took note and turned into these tips. Enjoy!

One of life's necessities when dating in your 40s.

Guys, are you having problems getting a second date with a lady? Do you ask yourself, “Why am I always struggling to meet women?” or “What’s the secret to getting past the first date?” or “Is there something I can do to improve my odds?” The good news is, yes, there are many things you can do. It took me some time, but here are the things I learned about dating.

For starters, it doesn’t matter if you’re heterosexual, homosexual, transsexual, or pan-sexual; you get good at dating by going on dates and learning the do's and don’ts. As a man, my expertise is in heterosexual relationships, so that’s the context in which I’ll frame my advice. (This blog post is perfect timing to coincide with today's historic SCOTUS decision on Obergefell v. Hodges; a victory for same-sex marriage.)

1. Time

Don't be late to the date. No excuses. Guys, we can have six months’ notice for a date, but we don’t start getting ready until six minutes before the date. She’ll already be a little nervous about meeting you for the first time and arriving late just adds to the stress. If you’ve never been to the place where you're meeting then get there early or reconnoiter it before the date. Don’t arrive two minutes before the date only to find that parking’s a problem. Amateurs think tactics, professionals think logistics. There’s nothing wrong with arriving 30 minutes early to read a book while you’re waiting. You’ll be prompt and look intelligent.

2. Dress

Dress clean. Wrinkled or smelly shirts don’t cut it. Dress sharp, yet appropriate. Grunge clothes, ripped jeans, and worn out shirts are fine if that’s you – but they still should be clean. Dress for where you want to go and make sure it’s appropriate. My pet peeve is seeing a beautiful woman, dressed to the nines at a nice restaurant with a guy in dirty jeans and a decades' old rock concert t-shirt.

3. Smell

You need to smell good, in body and breath. Shower as close to the date as possible, always within four hours of your date. Smell is important – very important. You have to love the way she smells and she has to love the way you smell to have a fighting chance. It doesn't matter if you’re smelling each other’s cologne, perfume, soap, detergent, hair, or simply each other; it has to be pleasant, and this is subjective. It’s part of the whole experience and less good smell is better than any bad smell. The name of the game is chemistry. Looking good opens the door, smelling good keeps you in the room.

4. Money

Guys, if you're so broke that transportation and dinner could break the bank then you may want to reconsider your dating options. Even modest, non-gold-digging ladies will find the fact that you’re a professional, white-collar adult and broke a turn off if they can sense it. Keep in mind, if you're going on a traditional date, that she'll probably expect the guy to pay. On the flip side, don't shower her with expensive gifts to show off your riches. That could make her feel like she’s being bought. Presume she wants to learn about you, not your money, three homes, boat or plane. Spending 200% of your planned budget on the date probably won't get you closer to the goalpost. Don't put a lot of pressure on your first date. Keep it low key. Lunch, coffee, or simply a walk are great options, especially if money’s an issue for you.

5. Food

Don't show up for your date starving otherwise you may get “hangry" when things aren't going perfect with parking, traffic, your dinner reservation, etc. Also, don't eat too much on the date. Nerves and disagreeable food don't go well together.

6. Drink

Watch your drinking. A couple drinks can lighten the mood and take off the edge. But don’t get sloshed or pressure her to drink more than she wants to. Also, if you think you’re only enjoyable when you're buzzed then you have to fix that before dating.

7. Talk

Talk little about yourself without being secretive or evasive. Let her dig out the fact that you're a millionaire CEO who used to be an astronaut. Actually, astronauts are the perfect role model since, when you meet them in a bar, they'll never tell you they're an astronaut (true story). They have the world’s coolest job and they’re genuinely the most humble people you’ll ever meet.

Instead of talking about yourself, talk about your date, listen to her, and be genuinely supportive of her thoughts and dreams. When a lady tells you about one of her problems on a date, don't try to solve it for her on the spot. Instead, simply listen. Listen. She's not looking for you to solve her problems. She’s looking for someone to listen and be her cheerleader. Don't try to fix her.

Keep the conversation upbeat and non-controversial. Everything you tell her will fall into one of three categories. Either be positive (“Did you see last night’s beautiful sunset?”), neutral (“Would you like to order dessert?”), or negative (“My landlord is such an idiot, he never fixes anything. The world is a trash can.”) Don’t focus on the negative issues in your life lest you be a Debbie Downer. It should go without saying that pontificating on politics, religion, or sex are a no-no for a first date.

Be honest. Tell her what you think, without being confrontational or opinionated. Tell her what you like about her, just a little. Don't pressure her with anything and don't play games: "She didn't return my call or answer my texts, yesterday, so I'm ignoring her today."

As a guy, it's not about being smarter or stronger. If you think you are, then move along. Seriously, if you're so much “smarter” than all the women you meet then do you really need someone "that dumb" to complement you? Let her see how smart you are by your actions. You don't need to tell her. If you continually find yourself dating “dumber” women then I’m betting you’re really the problem with your dates, not the ladies.

Also, don’t interrupt. People on a date get nervous. We all do since we're being judged. So chill out and let her talk all she wants. If she doesn't stop herself to ask you questions then that may be a warning sign for you.

8. Chivalry

She should have to discover your blessings by your actions, not talk. Don’t tell her how wonderful you are, she should see it. Open the car door for her except when the valet's doing it. Help her put on her coat or jacket except in situations where that would be obscenely awkward. When walking down the sidewalk, put yourself between her and the street without her noticing. Like a classical novel, filled with symbolism, let her discover that you stand for chivalry. You want to be thoughtful, not show-off-full. How thoughtful and selfless can you be without being a martyr?

9. Deception

No deception! Don't exaggerate your height or underreport your age. Starting off a relationship with deception is always bad. There are times when it's OK to lie, dating is not one of those times.

10. Endgame

If your date is going swimmingly then you might be the man she’s looking for, so continue thinking of her needs and desires. Be thoughtful. You’ll need to figure out her speed and match it. Too fast, with too much pressure for the next date, and you’ll scare her off. Too slow and she’ll drift away. The people you date will always be a mystery, at first. So, think like a Boy Scout: Be Prepared.

And always be a gentleman. If she was your daughter, would you want her dating a guy like you? If you want to kiss her at the end of the date then ask. Those are her lips, not yours. So, ask permission. You’d be surprised how much women appreciate the advanced notice to avoid an awkward encounter.

Remember that women want to be treated like the subject of love, not the object. To paraphrase Maya Angelou, people won't always remember what you say and they won't always remember what you do, but they will remember how you made them feel; so leave the ladies feeling lovely.

Finally, keep in mind that even if you do everything right it doesn’t mean it will always work out. Some things are not meant to be.