1. Whatever you do men…Do not mention sex until she does first!

a dating amber-colored man and woman lamp
Photo Credit: Michael Prewett

Please understand, women hate when we as men mention sex quickly….especially on the first date. So do yourself a favor, even if it is on your mind, do not mention it. Let her bring it up first. And let her lead the conversation. If she wants to talk about sex, let her talk about it. But do not continue to talk about it after she has clearly moved on in the conversation. Also, do not send her unsolicited pictures of your penis (like really? Men still do this and I hear about it all the time as a top 3 turnoff). This is the #1 way to get yourself deleted.  However, If she wants it? She’ll ask. Even then, I don’t recommend sending it. And whatever you do, do not ask her to, “Netflix and chill” or any variation of that saying.


2. Step up your clothing game

Next, there are tons of ways to take what you have in your closet and take it to the next level. First, get your current wardrobe tailored to fit you. Dozens of tailors are out there. And you don’t have to do it all in one visit. Spread it out. And if you have the budget, get rid of the over-sized clothes and wear your size. If you don’t know your size go to a tailor and have yourself measured.


On a budget?

If you have some disposable income, say… around $500, get a suit from a place like K&G. They’re always running a great buy one get one sale. Have them to tailor your suit as soon as you buy it. They have the same or within a day service. Make sure it fits properly. Not baggy. You can get a $150.00 suit and have it tailored and have it look like an $800 suit. Make sure it’s a neutral color that you can wear for almost any occasion. Smoke Grey is my personal favorite. Make sure you get French cuff shirts that are the right length and fit (slim or sport fit if you can wear those) and solid cuff links.

If you don’t know how-to, there are dozens of videos on YouTube on how to do different tie-knots.

Also, make sure you have at least one pair of casual and dress shoes that cost more than $100. And keep them very clean. Women look at your feet quite often.

Also, use the outlets to shop. You will save tons of money.

Try a website like Bluefly. They are great and one of my go-to shopping websites since I don’t like retail stores. You can find everything at discount prices from watches to 3-piece suits.


3. Step down your clothing game

If you wear jerseys, throwbacks, huge white tees, sag your jeans, wear shirts that are clearly too big (you are not an XXL or an XL sorry)…STOP! Grown men do not rock these on the regular. It’s OK [sometimes] for the game or when you’re at home relaxing. But as a regular wardrobe item? The answer is no!


4. Ask her questions, and make sure you listen and remember what she tells you.

men wearing a skull cap, while on his cell phone.
Photo Credit: Soren Astrup Jorgensen

Every woman I know loves a man who listens. But not just listen, but listens effectively and remember what she told him. So when you’re on date #5 you can surprise her by doing something she mentioned that she liked on date #1. Women love this. It shows that you are attentive to their needs and wants.


5. Pay until she offers to pay (never ask her)

Yes, the dating terrain for men is expensive. So make sure you’re truly ready to court/date a woman before you venture out. Meaning, make sure your money is where it needs to be before you ask her out. Nothing is worse than a man who asks a woman if she’s paying. Let her offer. And if you really want to earn points with her… turn her down politely with a smile and say… ”this one’s on me.”

On a budget?

That’s OK, you can still date. But you need to get creative. Try parks, coffee shops, festivals, cook for her, use Groupon and Living Social. Both websites have tons of savings on events, trips, movies, dining, and much more.

6. Let her ask you, about you.

Do not spend time talking about you. It shows way too much vanity.  Make the date about her.  And let her ask about you first. Then elaborate, but even then, do not spend too much time on yourself. Make sure you redirect a few questions after you answer.


7. Show your sense of humor.

men and woman in a field. Woman holding man from behind
Photo Credit: Shelby Deeter

Every woman loves a man with a sense of humor. Don’t be too dry or sarcastic. Pay attention to her cues. If she’s laughing, keep it going! However, if she’s not, develop a new strategy (and quickly). Whatever you do, don’t force-feed jokes to her. Create on the fly based on what you’re talking about. Let it flow! Make sure you laugh at whatever she’s joking about, even if it isn’t funny. Take one for the team if you want the grand prize.


8. Be a gentleman

woman holding her men hand
Photo Credit: Seth Doyle

Strangely enough, there are women who don’t care about this sorta thing. At the same time, most women love a gentleman. Pull out her seat when she sits down, hold all doors, and let her walk in first.

If your food comes first, do not eat until hers has arrived, offer to pick her up and let her know… “It’s OK if you’re not comfortable with me picking you up yet, but I wanted to extend the offer.”

Consequently, she’ll love that. Most men offer to meet up and you want to stand out from those guys. Bring flowers, or a card, or something creative that will show that you appreciate her time and company. Yes, we know your time is valuable as well, but you’re the man. Lead by example and make sure you are consistent.


9. Call her!

woman wearing a black skull cap, talking on her cell with her men
Photo Credit: Matthew Kane

We’ve all heard it before. “Why do I have to call first?” Well my friend, as men we take many losses when it comes to dating. However, taking this one for the team could translate to losing the battle but not the war. Women love an aggressive man who is proactive. Yes, I know there are women who play the game with phone calls, but you can’t worry about that. Just show her you’re interested and call her a few times a week.

Do not call every day, you do not want to seem annoying, you want to show interest. Do not text her more than you actually call her.

Texts are OK as short messages… and there are tons of women who appreciate the…”Good morning, how are you feeling this morning?…” text. But don’t make this your primary mode of conversation. Women hate this. And whatever you do… DO NOT ASK HER OUT ON A DATE VIA TEXT! Call her!


10. Take her out!

First and foremost, do not ask her to come over for the first date. Furthermore, even if you’re being genuine and not looking for sex, she will still think, you’re looking for sex. Take her out. Be original. Don’t just go to the movies or a restaurant. Go for a walk in the park and talk to her. Share with her, open up, and show her your vulnerable side. Don’t start crying or anything, but if you feel comfortable enough, share with her something that’s revealing (and not something that will scare her off). I’d save this for the 2nd or 3rd date (don’t be too serious on the first date).

Not sure where to go?

Museums are often overlooked but are great date spots because the exhibits can create conversations all by themselves and the atmosphere is quiet and without distractions. They are perfect for getting to know each other (and hear each other) Spend about 60% of your time outside the house. And the rest of the time doing whatever comes to mind.


11. (Bonus) Be Yourself! Be Confident!

Finally, ever since I was 11 and the girl at the arcade “dissed” me because I was “corny” I have always been myself on dates. I went to that arcade to play video games not talk to girls. But all my friends were doing it, so I tried. Needless to say, I failed, miserably. I wasn’t myself and I definitely wasn’t confident. I tried to act cool and it came off unnatural and fake. Trying to act like the other boys put me in the loss column (do you get where I’m going with this?). Women have a 6th sense for men that aren’t genuine. Be yourself and most of all, be confident, even if it doesn’t land you the girl.

There’s someone for everyone and understand you may take some losses before you get that win.