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HIM SERIES: Following Up With All My Single Ladies ( + Where To Meet A Date ) | By Michael

michael bosstick's HIM series | by the skinny confidential
michael bosstick's HIM series | by the skinny confidential

Hi, hi it’s me, Lauryn. HELLO.

This has been a VERY much requested post so I figured what a perfect time to post it because, FUCK, I’m sick. UGH.

Throat Coat & silver ( yes, silver ) on repeat over here.

In the meantime, my better, not as witty half will be posting on The Skinny Confidential tonight.

Anyway, we talked last time & I told you guys we launched the ‘HIM’ series so today Michael wrote a follow up post along with advice on where the hell to meet men.

( I mean I feel like if I were single, I’d just camp out in front of the library? Like ‘hey anyone got a library card?’ Really though, no thanks clubbing, creepy after hours clubs, or weird guy on a random dating site flexing the mirror with olive oil on your abs.

Ok, I’ll let Michael take it from here:

Hey Guys, Lauryn let me hop back on here to follow up with all of you on my last post!

I have to be honest, writing that last post gave me a little bit of anxiety which is really strange for me because I am really not the guy to get shy or nervous about speaking my mind ( as you can see if you follow my Snapchat, shameless plug: @michaelbosstick, hahaha! )

I really thought I was going to get my head torn off after that last one.

I debated softening it up or changing it around or making it less harsh ( does that make sense? ) but after I read it I just couldn’t and I’ll tell you why. I firmly believe in what I wrote, I lived a lot of those experiences myself. I have friends ( both girls and guys ) that are living them now! I have two sisters that I have constantly coached on these topics and I felt like delivering anything less than what I wrote before would be an unauthentic version of what I would actually tell the women in my life.

Am I 100% right on what I wrote? Probably not, but anyone that spouts off advice and tells you they are is full of shit. Do I believe I am mostly right? Hell yea I do! I firmly believe that the advice in my previous post can help the majority of single women in the dating circuit and that was my overall goal. To help.

michael bosstick's HIM series | by the skinny confidential

So now that we got that off my chest, did my advice help anyone? Were any of you able to apply these tips to your current dating situations? Were you able to help a sibling or friend? Did any light switches go off that provided insight on any of your past dating experiences? I would be really interested to hear if any of these things happened.

This brings me to my next topic, how do you meet the right guy?! Where do you meet him and what do you do when you do meet him?

First let me tell you that you can’t force this. If you are set on meeting someone quick and jumping right into a relationship, it may end up being a bad move. There are a lot of Mr. Wrongs out there lurking in the last call section of the bar waiting to pounce on desperation.

Just like business, you need to be patient.

You need to wait for the right moment. You will feel it when it comes but don’t try to convince yourself, just let it happen.

So what do you do when you see someone you may be interested in?

michael bosstick's HIM series | by the skinny confidential

First, I can guarantee you that we’re just as nervous as you. I got a lot of questions asking if it was inappropriate to make the first move on a guy? Yea, it probably is if you live in 1927. Lucky for you, you don’t.

If you see someone that you think you could develop a connection with, go ahead and approach. I personally think it’s rad when a girl takes initiative. What’s the worst that can happen? You get denied and move on with your life? Welcome to our lives. Or maybe it turns out to be something and all it took was a simple ‘hello.’ That being said you still need to make it a challenge after the approach, don’t blast in like a hungry beaver ready for war.

Second, can you guys please make it a little easier for us to know when you’re interested? Women do this thing where they expect men to know what they’re thinking. We don’t, we never have, & we never will. If you’re interested, make it known so that we can work up the courage to make a move.

So back to where you should meet guys.

This is a tricky question. I think that all depends on the type of person you are. If you hate night clubs and dive bars, then why the hell are you going to a night club and dive bar expecting to meet your dream guy? What about dating apps? Do you like guys on dating apps? Maybe, again depends what you’re looking for. I have heard horror stories and I also know people who have met online and are happily married. Maybe you will meet someone at the park? Or maybe on a river rafting trip, or maybe at a concert to save the whales. I DON’T KNOW! The point is, you will meet someone when you meet them and trying to set the stage won’t work.

michael bosstick's HIM series | by the skinny confidential
michael bosstick's HIM series | by the skinny confidential

I think the more important topic here is on not settling.

Be patient & get with the person that actually makes sense to YOU. Don’t settle for someone that doesn’t treat you right. Don’t stay in a relationship just to be in a relationship. What a waste of time! If you get lonely get a pet (or a Chihuahua, trust me they’re great ), hang out with friends, read a book!

But don’t settle.

When you do meet someone, take your time— develop a real relationship. Maybe think about some of the advice in my last post. I find that when I really force something, it usually backfires in my face. Life is funny that way. So take your time, be yourself, don’t settle and you won’t have to look for a place to meet someone. You will both find each other. I promise. It just might not happen right away.

Let me know what you guys want to see next, – Michael

SHOP HIM: black tee | green jacket ( similar ) | jeans | shoes ( similar ) | sunglasses

SHOP HER: black dress | sunglasses ( similar ) | shoes ( similar ) | purse ( << this one looks just like it too! )

{ photos }

michael bosstick's HIM series | by the skinny confidential

  1. Yesss! I think there’s no clear art form to finding the perfect guy but settling definitely comes into it.
    (Also, I love the idea of the HIM series!)
    xx, Pia

  2. This is just a great post series, and I am enjoying how you’re telling it like it is. I couldn’t agree more, DON’T SETTLE it took me 6 awful years to stop settling. Unfortunately I can’t get that time back–but I can resolve to be more confident on my own and never settle again.

  3. Love this post! Thanks Michael! Do you think a guy will go after you even if you’re not making it obvious you’re interested? If he’s super into you? Or do you think some guys need the validation that you’re also interested before they would make a move? I think sometimes women think it’s SO obvious that they like a guy and can’t imagine he can’t see that

    1. You’re welcome! I think it depends on the guy. My question to you is: if you are interested why not give him some kind of hint/clue that you are? why make it harder? What is obvious to women is probably not so obvious to men.

  4. I really enjoy the Him series and hearing from Michael! I’ve been with my boyfriend for a little over five years now and Michaels advice sounds exactly like what Colton would say to my friends lol.

    Love your relationship & TSC of course!:)

    1. Thanks Lauren! It’s funny how many guys think along these same lines but have a hard time getting the message across to the women in their life.

  5. Love this series even though I’m married. It’s fun to just read along! But seriously though – this advice mirrors EXACTLY what my husband tells my single friends. It’s truth!

  6. I’ve gotta say bossman, this post was ON POINT. All of it, from beginning to end. Perfection. I think the most poignant piece of advice in this post is that you have to be willing to meet people in your natural habitats, not in a scene that you’ve “set up” because you think it’s how it SHOULD be. Me? If it weren’t for my husband, I’d probably meet my dream guy in the business/personal growth sections of Books-a-Million 😉

    1. Tara,

      Thank you for reading and the compliment! I find it really strange when people try and meet someone in a setting they don’t like. What are they expecting to find there? Anyways… I like your idea of where to meet the right one.

  7. LOVE the post – and honestly LOVE your Snapchat. I have gotten so much extremely valuable business advice from your snaps – & I am about to turn into a major creeper with all the snapshots, but they are seriously that good. I, personally, would looooove a HIM series all about business – seriously! Your snaps alone could easily write a book, let alone a post!

    In a happy relationship here, but that said, how we met was not ideal. It’s all a long story for another day but it was more about WHO I met & the instant connection we had. To be completely honest, in my early 20’s, I spent a lot of time trying to convince myself I was an extrovert (it sounds weird, but it’s an easy thing to do at that age), so I was constantly going out to clubs/bars or places to be social, meeting people yes, but never quite clicked & it actually really attributed to my stress levels & anxiety – and I settled, a lot. When I finally realized that that wasn’t who I was (in fact, I’m quite the opposite and extremely introverted) it helped me associate with like-minded people and I’ve been happier than ever. The biggest thing is knowing who YOU are and then finding someone who complements that well, which happens seamlessly & will keep from settling!

    Great post & Lauryn, you are f’ing hilarious – LOL @ olive oil on abs…. At the very least do coconut oil, tinder dudes – that’s what us girls like! 😉

    1. Shannon!

      Thank you for reading and thank you for the SNAPCHAT love! I really like Snapchat because I can really be myself and showcase so many different aspects of my life on there. I am going to work on a whole series for business stuff. I just need to put it together the right way.

      I am glad you figured it out. Life is all about being true to yourself and not trying to convince yourself that you are something different. Cheers!

  8. Another great post! I love your simple advice “just be patient…just let it happen”. I swear the second I stopped looking for the perfect guy to date and started just focusing on me and what made me happy I bet my boyfriend of now 3 years. Crazy how things happen like that 🙂

  9. Patience is key, and that is something all women lack. Truth hurts ladies! We also settle far too much, but it is what it is. Anyways, your advice is 100% on point and something I keep telling myself after ending a great 5yr relationship and starting to “date” again. It’s honestly a fucking joke out there, so better to be alone and patient, then settle for nonsense!

    Love the snaps too btw.

    1. I agree 100%. Also, there is nothing wrong with being alone for a while. It’s a good time to reflect on yourself and what your goals really are. A lot of people get sucked into a funnel where they think they are doing the right things for themselves based off of others opinions only to find out later that they are miserable.

      Thank you for the Snap love!

  10. Great post! I definitely agree about not rushing things – I once started dating a guy ONE DAY after we met, which ended up in a turbulent almost-year long relationship and a broken engagement.

    BTW, L’s dress is killer!!!! Love how figure flattering it is (***opens online shopping cart while simultaneously doing my bombshell body guide work out of the day***)

  11. Second, can you guys please make it a little easier for us to know when you’re interested? Women do this thing where they expect men to know what they’re thinking. We don’t, we never have, & we never will. If you’re interested, make it known so that we can work up the courage to make a move.

    Love this part.

    I know for me, I had to SERIOUSLY pursue my babe (who I live with and have been with for 3 years) because he was shy, and again, doesn’t know what I was thinking unless I told him, or expressed to him that i liked him, was interested, etc.

    I know that good guys, don’t think that you’re into it – and they need a bit of encouragement along the way.

    They are just as nervous as you are – so patience is key, and doing your own thing through the process is also key. Do you – and will come.

    Loved this one – and meeting people is hard. I think often what I would do if I had to meet someone, I have no idea really. But not at places that I don’t frequent normally. like bars.

    xo to my fav couple.

    1. Thanks for reading Krista! The world is already hard enough. We don’t need to be playing the equivalent of battleship in the dating scene as well. Just give us a hint!

  12. You should do an advice column PS! answer a select number of questions each week about dating from the readers. I have a few myself !!

  13. I absolutely love the HIM series! Michael’s perspective seems so on point and it gels so well with your whole blog (you guys are obviously amazing together). One question though, in your last post you said to make a guy feel like there’s a challenge. You said not to be super easy or he’ll loose interest but in this post you mentioned making it obvious that you are interested in him. I feel like girls try to play it cool (i.e. provide a challenge) and then guys don’t know we’re interested. What’s the sweet spot? How do you let a guy know you’re interested without coming off like less of a challenge?

    1. Hi Sarah, check out this paragraph from the post:

      If you see someone that you think you could develop a connection with, go ahead and approach. I personally think it’s rad when a girl takes initiative. What’s the worst that can happen? You get denied and move on with your life? Welcome to our lives. Or maybe it turns out to be something and all it took was a simple ‘hello.’ That being said you still need to make it a challenge after the approach, don’t blast in like a hungry beaver ready for war.

      I don’t think there is anything wrong hinting to a guy that you may be interested. If he is too dumb to pick up on the hint, that’s his problem. That being said, once you start to date or he starts to pursue you, don’t make it easy. Make him work through the process and make him work to develop a real relationship with you.

  14. I loved your last post. Honest and so true. I’m not scared to approach a guy I’m worried he might be married, fiancé, or have a gf. Then I would feel bad/embarrassed about initiating a convo. I guess it’s not the worst thing in the world. My question is, what’s the best way to approach a guy and also find out if he’s not taken?

    1. Well… if he’s married or in a relationship and you approach him and hes receptive to the approach he is big scumbag. You just need to not come in guns blazing and jump right into something with him. If you have your guard up and spend some time developing a relationship, hopefully along the way you can figure out the truth. This goes into making it easy on a guy. If you make it easy you will probably never find out, but if you make it a challenge you most likely will. Also with social media today you should be able to find out a little about his life if you are pursuing a relationship with him.

  15. I’m loving the Michael cameos on the site now. I laugh daily at the Snaps so it’s fun to see his voice here too. Love you two, and totally get why you’ve been besties since you were 14.
    Much love and eating watermelon jerky (no really!) from Chicago…..xoxo

  16. These are great!! Can you do a post on how girls in a happy long term relationship can keep things fun an interesting? I love my guy, and I want to keep our relationship fun for the long term!

    Thanks! 🙂

  17. Seriously this post and the last HIM post were exactly what I needed to hear! I’ve been on/off with a guy for over a year and he most definitely does not treat me right and has never made me a priority. Basically more “netflix and chill” than actual dates. You’d think I would know better and tell him to take a hike (probably in more colorful language than that) but I’ve totally been doing just that…settling! Need to get it through my brain that if a guy actual gives an F about you he’ll make sure you know it. Thanks Michael I’m sure there’s lots of girls who need to hear this!

  18. Michael – LOVED this post – even more than the first one which I didn’t think was possible! After many many years as a single lady in LA I had finally started to come to some of the realizations in your last post. However, I was never sure if I was kidding myself or was actually onto something – it was so nice to have some of my thoughts confirmed and to also gain a few more insights!! Further, you answered a question I didn’t even realize I have continued to ask myself over the years in this new post: where can I meet guys? What do I need to do? Your answer is so painfully obvious yet beautiful in it’s simplicity – so thank you!!

    Absolutely love the HIM series, can’t wait to continue reading.

    Xoxo to you + Lauryn (it’s so cute to follow you both on snapchat and get the two perspectives!!)

    1. Liv, thank you for the feedback! When Lauryn asked me to do this I was really uncertain as to how it would be received. I don’t always have the softest delivery. These posts and these comment threads have confirmed to me that, although I may be alienating some, the others that I don’t alienate are really getting the message. That message is I am here to help, even if it’s just getting someone to look at something from a different point of view. Thanks for the support! I really really appreciate it.

  19. YESS! This post is everything and so so relevant! I ALWAYS tell my friends, never force it. What’s meant to be will be and if it doesn’t feel right then it probably isn’t. Although many of these things are easier said than done and sometimes it’s hard to see the big picture when you’re stuck in the middle. I believe men (and women!) are attracted to people who have their shit together, know what they want out of life and most of all, comfortable and confident in their own skin! Wonderful advice for all single women out there!!

  20. I. Love. This. Series.

    First off: Girls always get insight from their friends boyfriends, close guy friends, or people know them on a personal level, so it’s nice to hear some cold, hard, unbiased truth – don’t feel bad for saying it. That’s why everyone loves you and Lauryn (aside from you guys bickering on snapchat, which is hilarious), your opinions and personalities are real. Heavy, unabated delivery is what we’re all here for!

    Second: Even though the “ignore for attention but also show that you’re interested” game is tough to do, I get what you’re saying. I don’t like it. But I get it, and I’ll try it. You make a really good point in saying that if a guy is *actually* interested, you’ll know because he’ll show you. THAT’s what girls (or maybe just me) always forget!


    One thing I’d like to understand better from a guys perspective is “ghosting.” You mentioned it in your initial post. But being someone who dabbles every so often in the dating scene, I’m dead serious when I say: this is like, a PREVALENT fucking issue. If you’re looking for potential topics to discuss, I’d love to hear what you have to say about that.

  21. Hi Michael (and Lauryn! :)) I’ve followed TSC for years and I am loving the HIM series…I work in marketing and Lauryn, I think you’ve done a great job of slowly building interest around Michael (haha) to test & gauge whether or not your followers/viewers would have high engagement with more “manly” stuff instead of just slapping it on your blog and calling it a day. Seems like it’s really working!

    Micheal, I’d love to hear your thoughts on keeping things going once that post-honeymoon phase hits the relationship (whether it’s a few months or a few years). Asking for a friend….. 😉

  22. 2 things
    -act like a lady think like a man by steve harvey

    I met my other half at work. We were friends at first then started dating.. And when i say friends I mean FRIENDS. We also had the conversation of a future before we actually started dating like marriage, kids, living situation , etc etc etc… To some it’s to much to talk about before dating or an engagement ring but if you know what you want then JUST DO IT. I did it because I didn’t want my time to be wasted and well who does? It worked out perfect for us even though to some people it’s not normal, but i mean what is “normal”?
    On the other hand you don’t go looking for a man. It just happens. When you least expected. TRUST ME.


  23. I would love for the two of you to do a post on money management, money books (boss woman, or boss man), budgeting, how you go about saving for life, the importance of money in relationships (discussions, being on the same page), etc….! thanks 🙂

  24. Hey! I met a guy through this group that all watches football games together… he is really shy and we hardly ever talked, but I sent him a friend request on FB and he accepted (a lot of us in the group are fb friends). I want to talk to him on FB and hang out with him, but don’t know what, if anything I should say?! We will see each other a lot Sept-December, so I don’t want to make the group awkward… Should I say something, or let it go? Also, I’m 32, so I don’t really want to wait until September! 😉 I have been thinking about this for two months now lol..

  25. Just another dude’s perspective, because I 100% agree with all of your advice, Michael (found you two through Gary Vaynerchuk’s video, you guys killed it!).

    I’ve always met the most interesting and compatible women doing the things I personally love doing — fitness, cooking/food, traveling, French lessons, concerts, museums, football games, sports, etc….

    I don’t think it’s rocket science or coincidence that you’re likely to meet someone that’s like-minded and has most of the qualities you’re looking for when you’re just being yourself. Enjoy life, take the pressure off, do the things you love, put yourself out there, and you’ll find an amazing guy.

    Also, we totally love it when you approach us and show your interest. We’re not mind-readers, FLIRT IT UP! Just my opinion.

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