A man’s guide to getting a girl to like you

Hi Tiffany!
8 min readOct 6, 2015

Your welcome,
-a 27 year old girl who’s gone on 45+ dates in 3 years

YES, I get it — you want to sprint to 1st base, 2nd base, 3rd base of the dating stage…and ultimately score that home run. BUT don’t just jump out onto the playing field without warming up.

If you want to guarantee a 2nd date, 3rd date, or hell maybe the 20th date, you need to slowly get the girl to like you. It sounds hard, because most girls shield themselves with an invisible 3-foot brick wall. One wrong move, and good-bye! You’re permanently marked on her do-not-ever-contact-me-again list. But let me tell you, it’s actually stupid easy to break that barrier. Know how?

Treat the girl right.

Yup, that’s it. I promise you, she’ll text you the very next morning to ask how you are.

This is all you need to do:

1. Give compliments

Compliment a lot, ESPECIALLY on the first meetup. Girls love (sincere) compliments. It gives them that warm fuzzy feeling as if they’ve just hugged a long lost friend, and will definitely put a smile on their face. And don’t just stop with a compliment alone! 99% of the time, the girl will say “oh, thank you,” then silence. How to avoid that awkwardness? Follow up with a question or expand on the compliment. A good compliment would be something like: that outfit looks really good on you, where did you get it? Or wow, you look very fit. You workout at the gym? See how smooth that sounds? Remember, keep it cool. Be a conversationalist. Don’t be that typical flirt she has rejected for the 34th time.

Another word of advice: don’t over-compliment either. It’s a turn-off when we see you try too hard.

2. Pay for dinner

Sounds like a no-brainer, but you’d be surprised how many guys don’t (try to) pay for the girl’s dinner on the 1st date. And guess what that leads to? Not a chance for a 2nd date — I’ll bet my whole life’s savings on that. You see, when you slap your credit card on top of the check to pay, the girl will realize how capable you are as a man. It’s the equivalent of you taking off your shirt and exposing your 6-pack abs. It’ll give you a great first impression, but more importantly, it will boost her security that you can take care of her. Plus, you don’t want to sour a perfect evening by having her pull out her wallet and thinking you’re a cheap date. So be a man and just pay.

3. Offer to buy small treats

Ice cream. Coffee. Gourmet pastries. Caramel apples. Whatever it is, offer to buy her small treats. If she rejects the first time, buy it anyways (because most often, we’re too nice to express what we truly want). But if she really insists not to, then you can put your wallet down. Regardless of the situation though, she’ll be happy to know that you even offered. As much as we don’t like to admit, we love getting spoiled — to be treated as a princess — because it truly tells us how thoughtful you are and how you would do ANYTHING to make us happy. Naturally a sugar daddy at heart? Well, you’re already one step ahead of the game!

4. Chill! Don’t be uptight!

It’s in our blood, our DNA, to feel more insecure around guys. So if you jerk too much from being nervous or make any sharp anxious movements, you start making us feel very uncomfortable. Be confident, but relaxed— spread your arms out, stick out your chest, look at us straight in the eye (not at our breasts please!) when talking, lean back in your chair. But whatever you do, try not to show any signs of intimidation in our presence. Because believe it or not, us girls have this 9th sense that detects for weaksauce. This might be the toughest habit to break out from, but if you want to change your body to look AND feel more confident, watch Amy’s Cuddy video: “Your body language shapes who you are.” It’s 21 minute life-changing guide that will increase your chances of success — both for personal relationships and for work.

5. Make her laugh

This is, by far, the easiest way to make a girl’s “guard” drop down. You’ll get 2–3 more hours of quality dating time just because she’s enjoying every minute of your silly jokes. What seemed serious (the date) is now all casual fun. And that’s how all dates should be — fun and relaxing. You want to make the message clear that you’re a fun companion to hang out with instead of some sleazy guy who’s only looking to get into girls’ pants.

6. Ask questions!!!

A lot of times when I’m on dating apps (like Tinder, CoffeeMeetsBagel, Match, Skout, PlentyOfFish), I immediately stop talking to the guys that DON’T ask questions back. If you only answer without asking back, it boils down to one conclusion: you’re not interested. AND you’re probably self-centered. Unless you can manage to pull off something engaging, funny, or smart, don’t expect the conversation to last very long. Ask questions — show the girl you’re genuinely interested in getting to know her. That will automatically put you among the top 10% of the dates she talks to.

7. Ask engaging questions

Don’t be like those parents who always ask their kid, how was school?

But instead you ask, how was your day? How was work? — it’s the SAME shit! Unless she hasn’t dated much, a lot of girls would sigh with boredom and respond with …it was okay. I mean, what else do we say if you ask us this question every single day? It’s just simply unengaging, dry, and boring as fuck. And it makes it look like you have nothing else better to say. If you want to impress your date and blow her mind, try asking stimulating questions such as the ones in this dating conversation guide, “21 questions to ask a guy.” Disregard the title — they’re good questions to ask girls too.

8. Talk, talk, talk

Besides getting your first kiss rejected, the next worst thing you’d want is that 10-second awkward silence. I’m pretty sure this has happened to you — that moment where the conversation just dies, and both of you are panicking to know what to say next. Keep the conversation flowing by using these small, but effective tricks:

  • Ask questions about the last thing she said (it’ll be her turn to talk again)
  • Share a story, a personal experience, or express your opinions on the last topic (this often creates a deeper and longer-lasting conversation)
  • If you’re completely stuck on what to say, comment on your surroundings (and hope, this will spark up a new topic)
  • If all else fails, well, better luck on the next date.

9. Mention her name

Names are very personal. So when you say her name while talking, texting or emailing, it’ll grab her immediate attention. Whatever you say next will be 5x more meaningful and emotional.

Lily, guess what?! I just passed by this new coffeeshop that looks like a really nice place to work at. Think you should check it out.

Now, compare that without the name. Notice how much of a difference that makes? Try giving a compliment right after saying her name — it’ll sink into her head more deeply and make her feel even warmer to you.

10. Call her by a little “nickname”

Most guys call their girl: honey, babe, sexy, cutie, dear, sugar bear, sweetheart….girls love this! BUT if you make a unique one, that’s even better. For me, I used to be called “stupid cutie.” For him, I would call him, “silly putty.” No one really got the reason behind the nicknames we gave each other, but hey! That’s what makes relationships feel special, because no one will ever understand the true meaning of your names. Just you & her.

11. Appreciate her, ALWAYS

It’s easy to say “thank you” in the beginning of the relationship, but further down the road, we start forgetting those two precious words. Even worse, we begin taking things for granted. So remember to say “thank you” for all the nice things she has given you, said about you, or has done for you. It might not sound like much, but for her, she’ll see it as a very thoughtful note.

12. Use Smiley Faces

We like manly guys, but that doesn’t mean you have to avoid using smileys or emoticons to express how you feel. You might think smileys are only used by girls or wusses, but actually they make the girl feel more connected to you because she’ll naturally see that you’re always happy. And that will make her more excited to talk to you. After all, it’s more enjoyable to talk to someone who’s more enthusiastic, right? :)

13. Work with her, good times & bad

If she’s struggling with a problem and needs someone to talk to, don’t just brush it aside/ignore it and carry on with your day. I know it sucks to deal with other people’s problems, but if you can’t be there when she needs you most, how can she trust you in the future? If she’s worth your time, do what you can to support her. It’s a small sacrifice to make on your part, but if you can straighten problems out, she’ll know she can count on you for anything, through good times and bad.

But if you’re in the middle of something important — like preparing for your business meeting or attending your friend’s wedding, let her know that you care and you’ll get back to her once you’re free. She’ll understand.

Golden Tip: Choose a pleasant spot to eat at

There’s a reason why fine dining restaurants or places with a nice atmosphere can charge a ridiculous price for their food. Because you’re really paying for the ambiance. You’re paying for servers who know how to treat customers right. Simply put, you’re paying for a great night. Choose places with dimmed lights, that are nicely decorated, and packed with people. Or if you prefer something other than high-end restaurants, try a DIY BBQ or a hot pot restaurant. What’s more fun than cooking, chatting, and eating at the same time?

But if not dinner, find a chat-friendly place to have some coffee or tea.

Remember, girls need time to open up. If you push too forward and it’s blatantly obvious, you might as well call it quits. Because in most dating cases, first impressions become your last.

Play it smart, not fast.

You’ll be surprised at the results.

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Hi Tiffany!

Walking through the second chapter of my life by asking: What can I do for the world? You’ll find the answer at http://misstiffanysun.com/about