The Complete Guide to the First 30 Days of Dating

Relationships are hard to come by and even harder to make work in the long term. For some people they are a mystery too obscure to solve. In the service of those who want to walk the road to long-term intimacy, we’ve detailed the steps that will help you navigate those fraught first four weeks. Maybe the relationship isn’t right and is destined for nowhere, but you also may have found a keeper, and your actions aren’t lining up with your intentions. Emily Morse, sexologist, author and host of the Sex with Emily podcast and weekly co-host of nationally syndicated radio show Loveline with Dr. Drew Pinsky, believes that you should stick to your commitments. “Women want a man with a plan who is decisive and follows through. Demonstrate you are a man of your word.” Ultimately, women are looking to see if you are going to make a good boyfriend, and possibly husband and father. “Women are like detectives. We remember every single thing you say,” says Morse. “We are paying attention, so be honest, truthful and show who you are. Women want a man who is patient, kind, interesting and interested. Also, remembering things she says shows that you don’t just see the woman as a sexual object, which is important.” So, here is some womanly wisdom so that you may be saved heartache and possibly some drinks to the face.

Week 1: First Contact

Week 1: First ContactThe first week is probably the most intense part of dating. You need to determine if you like the girl you are dating and, well, if she likes you, too. For that to happen, you need to communicate. “Follow up after the first date, tell her you had a really nice time and show her you are interested,” says Morse. “I don’t believe in the proverbial waiting three days and playing games. I wouldn’t resort texting or anything, either. Get to know each other in person, because I think people prematurely escalate over text before they even know each other. I would try to keep that to a minimum and make a real date.” Here’s advice for those first days together.Be yourself.Never try to be someone you aren’t. The truth always comes out later. If a woman doesn’t like you for you, she’s not worth another date.Take her out.I know this seems self-explanatory, but many men don’t do it. The first date shouldn’t be cooking in your house. Maybe the second or third date would be okay. But you need to start things off at a public location. It’s also great to show her some cool spots around town. She will feel inclined to show you some places or activities she enjoys, and you may find you have even more in common than you knew.Smell good, look good and be confident.Please do not show up on a date in sweats. Look at least like you tried to care about what you are wearing. Women like confident men, but not cocky men. Take care of the first few meals and transportation (if necessary).I know this is old school, but the truth is you should still pay for the first few dates. A woman usually won’t mind paying or splitting the bill later on, but you should demonstrate your generosity. Or at least that you are not cheap. Also, it’s important to make sure that she gets home safely (especially if she’s had a few drinks).
Week 1: Second, Third Dates

No cell phones.This should go without saying, but put down the damn phone. Live in the moment. She should be the most important thing. If you absolutely must use your cell, let her know before you need to do it. It’s the polite thing to do.Make eye contact.Stop staring at her breasts. It’s not cool. Looking into a woman’s eyes lets her know that you are interested in what she has to say and that you are focused. Wandering eyes mean wandering mind.Ask questions.If all you do is talk, you will never get to know her. Ask lots of things about her: her interests, her past and her ideas. But don’t inquire so much so that it feels like an interrogation.Do not Facebook her.You shouldn’t ask to be a Facebook friend in the first week. Same goes for any other social media. You’re starting out a stalker. Carry condoms.Don’t assume anything. You should be able to afford these or get them for free at a clinic. You don’t want pregnancies or STDs, and you never know when you’ll get lucky. Later on, you can talk about other forms of birth control.
Week 2: Getting to Know Her

This is the week of getting to know the girl you met, making more of an effort, rearranging your schedule and finding some cool spots to take her. This is also the time to show her what a great kisser you are. “Be a good listener, ask questions, be conscientious and demonstrate interest,” says Morse. “Take it slow. You should plan an outing somewhere or a daytime date that’s lighter, easier and casual. Don’t get overzealous when getting to know them. Don’t make plans for the future just yet. Women want a guy that is into them, but you don’t want to be too overbearing because that’s also a turn-off.”Don’t go overboard.You don’t need to take her to the fanciest restaurant, pull up in the nicest car or jet to Europe. Women are more impressed with small gestures that let you know you care. Be a conversationalist and ask questions. You could attract a gold digger if you lead with your wallet and grand gestures that don’t mean anything.Make her feel special and compliment her. (Be specific.)The lamest thing you can tell a woman: “You are so beautiful.” Find a new line. Something that pertains to her as an individual. Try using compliments like, “I love the way you laugh,” or “I love that you have a dimple each time you smile. It’s adorable.”Don’t talk about your exes yet.Who wants to hear about a past relationship in any capacity during the first few dates? Let’s face it: Women are jealous and want to feel special. You can tell us about exes down the road, but, for now, stick to the basics. 
Week 2: Better Dates

Take her on a date that involves neither drinking nor eating.Especially by the time you get to a second or third date. Sometimes it’s nice to not get shitfaced or talk about all the fine cuisine in front of you. If you don’t have loads of cash in your wallet, take a nice beach trip or go to a nearby museum. Sober usually is the best way to get to know someone. If you or she had one too many drinks on the first date because you were nervous, make up for it with clearheaded conversation.No bodily functions.Wait to fart and burp in front of her until after the first couple of months. We all know you do it (we do, too), but you can refrain.Make an attempt to be mannerly, but don’t overdo itBy all means, open a door for a woman, pull her chair out or offer her your jacket if she is cold. It’s thoughtful and doesn’t go unnoticed. Just don’t act like her butler. She’ll get spoiled and clingy and will always expect a servant.Lots of attention paid to the lipsKissing is sexy. Good kissing is sexier. If she’s a bad kisser, it’s probably time to move the hell on.Touch (but don’t maul) her.There is a fine line between being playfully physical with a woman you are into a woman and pawing at her like an animal. Women like to be touched, but not groped.
Week 3: Getting to Know Her, Part 2

This is the time when you stop putting all your energy into work and making money and actually devote some time to her. Let her know you care. Don’t be judgmental. Morse believes that it’s important to talk about yourself, show that you know you and that you want to get to know her, too.  The issues you have on the third date you will have forever. People waste so much time thinking they are going to change someone, but you shouldn’t try this. You can’t change character traits. “The conversation can get a little more into what you guys are looking for in life and your futures. Maybe getting more into your personal background, your family, what’s important to you and delving deeper into what your values are,” she says. “These are things like: does she like her job, does she have healthy relationships, and is she happy about her friends and her life?”Make yourself available.We are all busy, but being too busy is a red flag that work is the most important thing in your life. It shouldn’t be if you’re looking for a long-term relationship. Do you want to be single forever? Find time in your schedule to include her. If you are into being committed, you will find the time. Casual does not mean uncaring.Just because you aren’t exclusive yet does not mean you should act like the woman is not important. Casual can be fun, enticing and feel good. But you should also make spending time with her a priority. If you really think she doesn’t deserve it, let her go.Be honest and open.Your female friends might have told you to wait a few days to text or call your date. But why? Don’t be annoying, but you can certainly follow up and say that you had a nice time. Women like to feel appreciated, and they don’t like guessing if you like them or not. It’s okay to ask for another date after the first one. And waiting a week is too long.
Week 3: Lose the Judgment

Give her a fair shot.Not every relationship will be like your previous ones. Treat each woman like a new beginning. You can have some reservations, but don’t act like she’s the next girl waiting to break your heart. Give her a chance.Call and at least pretend to be interested in what she has to say.The key is to listen. The only way you are going to know if you like a girl is if you actually know she has a brain and can communicate. She might tell you the most boring shit imaginable, but at least pretend that you care. Do nice things without expecting something in return.Be thoughtful. Women like to receive presents and know you are thinking about them. Just a thoughtful text or cooking her favorite dinner is a nice gesture. You shouldn’t expect anything in return, but being nice and supporting her with love is a sure way into her heart.”Group dates” are not real dates.Hanging out with friends is great, but you need to be alone together. I suggest that friends should not be involved until after the first month. Before then, get to know a little about who you are dating. The friends will come but, for now, chill. Group dates in which half the party is strangers are a bad idea.
Week 4: Real Connections

By the end of the first month, it’s acceptable to see if you are sexually compatible (if you haven’t already done so). But make sure you both are on the same page.  Let her know your intentions and don’t lead her on. Be honest about your feelings with her. “If you are paying attention and your eyes are open and it’s not all about alcohol, you should know,” says Morse. “The wrong thing to do is just agree with everything she says so you can sleep with her.” When it comes to sex, Morse doesn’t play the numbers game. “I do think that sex is better the longer you wait,” she admits. “When you have sex too soon, you tend to focus on the sex and not the relationship. We tend not to see potential issues because you are in the lust phase — and the chemicals, the dopamine, the cortisol, the adrenaline — all that stuff is spiking so you are thinking you are really into this person, when really you just become attached to the sex,” she says. “For women, our brain is our largest sex organ. If we don’t feel connected with a man emotionally, we don’t open up. So the more you reveal yourself, the better able you are to connect on deeper levels. That’s how we process attraction.”If you are seeing other women, tell her.Be honest. You don’t have to tell her that you are sleeping with five other women on your first date, but don’t two-time her. Women like honesty. And if you start to spend more time with her, you need to make a decision.Laugh, and try to make her laugh, too.You don’t have to be the next Louis CK, but not everything has to be so serious. Getting a woman to laugh is sexy. Just don’t be too corny. That’s a turn-off.If you don’t feel a connection, move on.A connection is essential to any relationship. You need more than a physical connection to sustain one. Attraction is great for the first few months, but if it doesn’t progress and evolve, it will inevitably die. If you aren’t feeling it, you need to communicate that. Otherwise, you will just be friends with benefits. Hot sex without a deep connection will never last. Do some soul searching and figure out what you want. Dr. Morse suggests jotting down notes and thinking honestly about whether you could get serious with this person. Then, have a conversation about it, and, if you are on the same page, move forward. Remember: there are always two people (at least) involved in any relationship. If you know it isn’t working, don’t waste any more time.
Week 4: Rules About Sex

Make sure she climaxes, too.Try not to get off and then go to sleep. If you don’t know if the woman had an orgasm or not, ask her. Hopefully, she will tell you the truth. You should be as invested in her needs as you are in your own. Be an attentive lover and give back. Always return the favor. She will appreciate it. Sometimes though, it is hard to get a woman off vaginally. Ask her for some pointers if you can’t figure it out. Don’t pretend to like her in order to get laid.Sex is great, but not if you aren’t on the same page. If the woman is really into you but you see her as a sex buddy, there’s a problem. Be upfront about your intentions. Who knows? She may feel the same, but have been hesitant to admit it. Better to know what’s going on, for both of your sakes.If you aren’t in the mood for sex, explain why.Some of you may be thinking, “When does this ever happen?” But there are times when you drank too much and can’t get it up or you have a big day in the morning or you’re just too tired and can’t get into sex headspace. Whatever the case may be, please explain what’s going on. Otherwise, we think we did something wrong. That’s never a good thing.Don’t score and run.If you are willing to use the bed for sex, use it for sleeping next to her. I don’t care if her bed is uncomfortable, it’s too loud outside or you enjoy sleeping alone. Women like cuddling afterward. Get over it.