Relationships Etcetera
dating men and woman in a field sitting next to each other laughing

10 Tips For Men To Help You Shorten The Dating Curve

January 17, 2019 0 Comments

I wanted to create these 10 dating tips because I definitely understand all the trials and tribulations of dating and what men go through (as well as the ladies).

Contrary to popular belief, a man that is looking for a wife or serious girlfriend doesn’t really like dating. But it’s a necessary... so, we do it.

For the men who find themselves constantly failing with the ladies or the men who are considering getting back out there. Here are a few tips for you that will definitely boost your ability to seal the deal.

You may feel you don’t need help… and if that’s the case, just read this for entertainment purposes or share it with someone who you know who could use it. But I believe there’s something in here that can help any man.

In no particular order…


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 great buy one get one sales. Have them to tailor your suit it as soon as you buy it. They have 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 a 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 remembers 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 men 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 woman 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 a 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 the 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 in 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.

Jay Thomas

Yeah it's true... I'm the ultimate blogger/writer/bad boy/urbanite/thinker/philosopher. (yeah...all those) No matter what happens, at the end of the day I’ll make you smile, laugh, and wonder, “How come I’ve never heard of this guy's blog before??!!” Want to know more??? Read more (hint hint) and make sure you leave a comment :) Are you still here? Well, come on…I’M YOUR GUY!!! YOU NEED THIS BLOG in your life!!! Oh and yeah...Don't forget to subscribe!



get coaching