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Five Major Dating Milestones For Men

In the early stages of a relationship, men have their own milestones. It’s not to say women don’t have the same ones, but what has a tendency to happen is some women get caught up in these moments that are important to them, then are surprised to see their man’s nonchalant reaction to the same moment. They think the man isn’t taking things as seriously as her or didn’t feel the gravitas of whatever just happened.

Not true.

Some men just don’t see the same big deal a woman sees. For some men, their big deals come at a different time. And let me add, before I get into exactly what those moments are, I know this isn’t all men I’m talking about here. This is just some of them and some women, as well, might agree these are milestones for them too. So here it is, the five major dating milestones for men.


The first kiss has always been a dating benchmark. Even some men are waiting for the moment to lock lips with the girl they’ve been dating. Nine times out 10, it’s going to happen when two people say goodbye to one another, but a first kiss goodbye says little to nothing at all. A lot of times, it’s a formality of sorts. But what’s not a formality is locking lips with someone upon greeting them. Kissing someone hello is a game-changing statement because it’s speaks volumes more than a kiss goodbye. All a kiss goodbye says is, “I had a great time with you tonight.” A kiss hello says, “I plan to have a great time with you tonight.”


I actually think this is something men and women can agree upon, but we certainly don’t act like it. When either gender goes out on a first date with someone they really, really like they set the bar so high, they almost cannibalize themselves. Let’s calm down people.

The first date is to give me a better sense of the woman I asked out on a date. The second date is to see if the things I came away liking on the first date still hold true. And the third date is to say she passed the previous two and now some real fun can begin. If I date a woman for the third time, 100 percent of the time, I’m doing it again, as opposed to the first date (50 percent) and the second date (75 percent).


Who cares if I can hang out with a girl in private? If we’re in our own homes, acting civilized and getting along, that’s great, but at some point, we’re going to leave our respective lairs. Together. What’s going to happen then? Just because the woman I’m dating can enjoy  a nice bottle of wine from the comfort of her couch, and doesn’t act up, does not mean I can take her out somewhere to do the same thing. She can actually be the type of woman who stands up on bars after about two glasses and the only reason I didn’t know is because I don’t have a bar at my apartment. I believe a couple who can party together, can chill together, but a couple who can chill together, isn’t necessarily as versatile.


Don’t get me wrong, my mom, sister, and grandmother must still co-sign a woman I care about, but there is nothing like the co-signature of my closest friends. The thing is, I spend more time with my friends and see my friends more often than I see my family, and though most of that is based on simple geography, a lot of it is also based on how I socialize.

Chances are, I will probably have to split more time between my woman and my friends than a woman and my family, but if I had a woman my friends actually liked, no time needs to be split. Also, the way my friends know me as a man is more accurate than the way my family knows me as a son, brother, and grandson respectively. In other words, my mother, sister, and grandmother will co-sign a woman based on what they think is best for me and if I disagree, they will let it go because it’s what makes me happy. My boys on the other hand will co-sign a woman based on what they know is best for me and if I disagree, they’ll say I have no idea what I’m talking about and bring something up from my past to prove their point.


This may sound weird but the more I like a girl, the more self-conscious I am about the first time we sleep together, and the only reason I feel comfortable saying this is because I know a lot of men feel the same way. Most women wait until they’re comfortable with someone to sleep with them, most men get comfortable with sleeping with someone. Though I’ve had some great first times, the second time has always been better, even if the first time was good. I may never get a chance to make a first impression, but I should be given another chance to blow that first impression out the water.



Did some stretching this morning, and some push-ups and crunches; thinking about meditating. Any tips? Also, who has some good habits to stop checking email so obsessively?

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  • Jessica

    Yay. First 🙂 Sending this to my boyfriend!

    I really cosign the point about Private vs. Public time. Thinking of my past two relationships now, and also looking to some of my close friends’ relationships for validation, it’s so true that the couple that can go out and dance, laugh and be merry in the presence of others really goes far. It’s a difficult thing, I feel, for most people to master how to treat their significant other in the presence of others- an interesting mix of not all the way friend, not all the way lover- and it helps if you and your partner are actually friends 🙂

    The cosigning of a guy’s friends is also something that can’t be overlooked. Just like you said in another post, we want to meet them too, not just to make sure they think we’re excellent for you, but to also make sure they aren’t hos who will encourage you to cheat! 🙂

  • Truth

    The kiss hello…I like that! I never thought of that. Sooo true!

    Great Post!

  • AS

    As far as meditation, there are a few different schools of thought (no pun intended) in the Buddhist tradition. I’d recommend doing one of two things(or both).

    1. Hit the bookstore. There are a lot of good reads on the subject.
    2. Visit your local Zen center.

  • **inquiring mind**

    Interesting list, in a good way… Anyway, about the pro-sess… hmmm. I think meditation is good, very good actually. However, when I meditate it’s more praying if anything I think. I usually take that time to have a conversation with God (I’m a believer *shrug* soo yeah, I talk to Jesus) about whatever is on my mind, not necessarily asking for a blessing or whatever just kinda uttering my thoughts to Him. I did this a lot when I took yoga… most times I just ended-up repeating “thank You” over and over again… it was very calming.

    Habits to stop obsessively checking email? (I should know this one)… hmm, nope nothing. I guess it depends on why you’re being so obsessive. To that I ask, “Well if it’s something important you’re waiting for, then what’s the big deal… be obsessive” and if it isn’t important “Can’t you find something better to do with your time? Go make/build something”.

  • AS

    Regarding the checking of email: I’d strongly recommend shutting off your alerts, whether this is to your blackberry or smart phone of choice or home computer. I had to do this at work because I’d literally stop what I was doing to check every email that arrived.

    I try to check once every hour or half hour. But not checking every time something comes has increased my peace of mind and productivity.

  • Tasha

    Great list! I like the idea of the kiss hello. Never even thought about it that way. Makes me smile……..

    I tend to check my email via BlackBerry so I usually put my phone on vibrate to avoid checking them or getting notifications that are almost always non-urgent or life changing. As for meditation, music in the form of Anita Baker or Bilal do the trick every time in the evenings when I get off work. In the morning I meditate by listening to the same gospel song on repeat and doing 3 yoga poses/stretches. Non traditional but it gets the job done.

  • P.A.

    Tip for not checking email—disable it from your smartphone. I had a Sprint situation where I to get a temporary phone and did not have email access for like a week. The first three days I felt really paranoid/frustrated/guilty for not reading/responding to emails as they came in, but then I became more regimented about checking email in a schedule (based on when I had access to my laptop, etc.) and when I saw people werent busting me out for getting to them in 4-8hrs instead of 5 seconds I calmed down.

  • MissMina

    Those voice guided meditation CDs are a great place to start. they talk you through the process of getting to the right state of mind and provide background music/ambiance. Once you get it, you will be able to get to the state on your own. Its really pretty simple and sooooo relaxing. I need to get back into it myself.

    Its funny you ask because I am working on a project for my thesis where I will be creating a website based on the Subconscious mind. And one area of the site will be a “Meditation Room” where one can control the sounds of nature and do a guided meditation online. I’ll keep you posted, coming soon in 2012! Lol

  • Alice Everleigh

    Love the list. Most of it applies to women too. My favorite is the last one. The first time is awkward at best. You are still feeling each other out (pun totally intended). Neither of you are sure what the other likes, how far is too far, where to slap as opposed to where to tickle. Unless there is some really hungry passion (or alcohol, which is sloppy for the first time) then you both usually hold back and err on the side of timid. The second time is usually exponentially better.

    For meditating, I would start with yoga first. If you can empty your mind while doing something relaxing with instruction, it would a much easier transition to empty it while doing nothing at all. Sitting still is more stressful than you may think.

    As for e-mail, unless you limit your access you’re screwed. It’s the same as the good old days of (only) snail mail. We all ran to the mailbox, even if we were just kids, in hopes that our name would appear on something. Now we get to get that rush like a gazzillion times a day. Between work and personal emails, facebook messages, twitter tweets, IMs, texts, BBMs….it’s amazing we find time to pee! It’s become a addiction. You are not alone. Perhaps you have to stop exchanging emails with such interesting people….

  • Nadira Rae

    You can try this for a mediation exercise: first sit on the floor in a quiet space (door, windows closed, etc). Initially you can have on some light mellow music (jazz or classical, nothing with lyrics) or some nature sounds playing (waves, etc). This is just to relax and wind down your thoughts a bit. Then when you’re ready…turn off the audio. You need a bowl of water and some salt sitting next to you. Pour the salt into your hand and just think of all the thoughts and stressors that you want to let go. The salt represents all those things (you really want to feel like you’re transferring those thoughts and everything into the palm of your hand….really try to clear your mind…completely). Then when you feel like you’ve reached the point where your mind is clear and at peace (transfered all your thoughts), release the salt into water (letting everything go).

    At this point you can stop or just sit and focus on your breathing, and keeping your mind clear. I’d recommend slow, deep, breaths (in the nose, out through the mouth). When you exhale, make the sound like you’re trying to see your breath when you blow it in cold air (like a ‘haaaaaaaah’…it should be just as audible as when you’re inhaling). Really concentrate on every breath you take as it breathing life into your blood and traveling to every organ and permeating every cell in your body. Really feel each breath as a life force (all the while keeping your mind CLEAR).

  • Nadira Rae

    You can do them both together, or just one exercise…or none at all if it’s not your cup of tea lol. Good luck!

  • HoneyMoney

    Jozen, I’m so 50/50 on liking your posts. This one I like! And I agree, with the second time having sex thing. Its almost always better!

    As for meditating, everyone has given lots of good info here for that…Mine is Yoga. Its ok for guys to do Yoga now, I swear! I see them in class all the time…the reason I suggest this is because you want to check your email all the time. I have this same problem bc I work from home/freelance. I have a hard time meditating in my own home bc there are so many distractions. Taking a 60-90 min yoga class forces me to be in an entirely separate place. I feel like I get myself into a meditative state when I am practicing and its helpful for me bc I’m too antsy for sitting meditation. Doing Yoga forces me to allow myself to be in uncomfortable positions and just be there. TRY IT!

  • NellyBean

    Great list

  • Netreia

    “A kiss hello says, “I plan to have a great time with you tonight.””–LOVE IT! You nailed this one for me.

    I tried the meditating thing, but my mind is too overactive for that. I end up just thinking about random things like “Man, I love beautiful, sunny, cool days” and “What am I eating for dinner” LOL! But hey, to each their own right…

    On checking email, if its on your phone turn-off the automatic updates/alerts…if its your laptop, shutdown completely when you’re done…

  • Aisha

    I co-sign this list. The kiss hello and the second sexual experience are on point. I meditate and some great advice has been given. I focus on my breathing pretty much til my mind is clear and just listen to God. It is very peaceful and eliminates stress. Yoga is great too. You have to force yourself to do it though so it becomes a habit and easy to do.

  • wahoo4uva


    Here’s a link to a beginner’s guide to meditating. It’s from a blog I occasionally read called Wake Up Cloud.

  • AlesiaMichelle

    #1 #1 #1…
    Europeans are all about the greeting with a kiss. We as American are not up on that. This is also a clue to see if I really like a guy. A kiss ‘goodbye’ is common. A kiss ‘hello’ is rare, and almost never bestowed.

  • brownivyx

    I love this post, and it’s seasonally appropriate as the weather cools down and people start to pair off lol

    One of my favorite parts of relationships is that physical familiarity, when the tension of posturing and awkwardness gives way and you really start to become a part of each other’s personal space. As such, I love the kiss hello. Well, I enjoy the whole dance of “hello”. That look in his eyes when he first sees you…the same look you can feel being reflected in your own gaze. The catch of my breath as we close the space between us on the way to each other from two ends of the room. And then, the full on body hug, accompanied by the kiss; taking in his scent before we pull away.

  • Kady

    I like this list! didnt realize the kiss hello is such a massive statement but it really is. Meeting friends is really important to me, I think it says so much if a guy doesnt introduce you to his friends. Other random thought the 2nd time you have sex should immediatly follow the first time you have sex. One of my favorite first is the first time a guy reveals something personal, something he is insecure about or a secret that not everyone knows, i think its so cute.

    Tip for checking email less often: I have a droid and I turn off the automatic sync, so I have to manually open my email and sync it, i realized that if I dont see those little message icons popping up, then I’m really not that inspired to check the inbox.

  • SwwooWoopBlooded

    Meditation is key! For the answers in life you got to ask the questions, and meditation is the most supreme form of question answering/ problem solving. My advice would be to go into it in earnest with strong purpose. You may benefit less on sum “hmm im bout 2 try this out”
    Email- set your settings so you only receive mail at certain emails; every 3 hours or whatever. Or do an email fast, disconnect the accounts from your phone just so you can begin to remember what its like without it… Then plan implement further discipline upon returning to its use There’s nothing to get you back in touch with reality like loosing the fiction 😉

    Peace and Abundance

  • Enrique tu amigo

    There are varieties of bottled water but for the most part you get the same substance. This also applies to meditation. In The Relaxation Response, Herbert Benson asserts, “It is important to remember that there is not a single method that is unique in eliciting the Relaxation Response. For example, Transcendental Meditation is one of the many techniques that incorporate these components. However, we believe it is not necessary to use the specific method and specific secret, personal sound taught by Transcendental Meditation. Tests at the Thorndike Memorial laboratory of Harvard have shown that a similar technique used with any sound or phrase or prayer or mantra brings forth the same physiologic changes noted during Transcendental Meditation: decreased oxygen consumption; decreased carbon-dioxide elimination; decreased rate of breathing. In other words using the basic necessary components, any of the age-old or newly derived techniques produces the same physiologic results regardless of the mental device used.” There are six basic instructions to eliciting the relaxation response from meditation as developed by the group at Harvard’s Thorndike Memorial Laboratory and I will not list them here. That is what the book is for (it comes highly recommended) and you can find them on page 129-130. However, Jozen you know me so just holla and we’ll chat. DB!!!

  • Bebe

    You gotta read the 4 hour work week Jozen. You check out the blog too. Plenty of tips there.

  • leressa

    I like the list.. I had never really given any thought to a hello kiss… I have given hello hugs ( the church hug) lol, but never a hello kiss , now that I think about it. I also agree with the all the other important dates that you mentioned. Glad to know that those things are important to men as well.

  • TMaria

    Really good list. I do not think I have ever given the hello kiss just the hello hugs and even that took a while for me to get there. I am a former church hugger and apparently guys are offended by such acts. I have since changed. Public time vs private time is very important as well. It is a good way to find out if your new boo can be social or if they are crazy deranged and most importantly whether they have jealous tendencies. As for the 2nd go round yes can speak volumes. Most women give a past for 1st time jitters.