How not to date in your 30’s – 16 tips

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When I joined the dating world in my 30’s I was seriously pumped. I thought, I’m finally confident, I can afford to dress the way I want, I’m in shape, I’ve got a house, I’ve got my shit together – this is going to be a blast! I had one tiny insecurity that men wouldn’t want to date a divorced girl with kids, but that insecurity was quickly debunked. In the beginning I was excited that there was a bazillion dating apps and websites, thinking “This should be a piece of cake!” And it was a piece of cake to meet a bazillion odd men who I would never go on a second date with. (Accept for that one amazing guy who had 6 kids and wanted more – that small detail was NOT on his profile, otherwise he was a great Brady Bunch match). So after trying – get ready for this confession of a single mom – ALL the sites and apps including: Bumble, Tinder, Plenty of Fish, EHarmony, Match, Meet Mindful, Law of Attraction Singles, I got pretty bummed about not meeting someone I was really into with the exception of the Brady Bunch dad. Someone once said, “Well it’s a numbers game – just keep going on dates.” But it’s honestly very time-consuming, exhausting and sometimes feels – well -desperate.

“Dating in your 30s is like trying to find a good parking space. All the good ones are taken and the only one’s left are Handicap.” – Says my ex husband.



On top of the dating apps, I would occasionally meet a guy organically when I was out with friends. As we mostly go out to restaurants with bars, we primarily met what I’ve come to learn are called “fuck boys” –  aka players. Usually very clever, very good looking and well built. Typically unreliable in one way or another – like rarely responding to texts, canceling plans, being vague about future plans. The truth is they’re “just not that into you”. Because if they were they’d make you a priority. They are, however, very charming. Because they’d definitely like to fuck you – thus the name “fuck boy”. This is at least my humble interpretation of this phrase which the most credible online source, Urban Dictionary, defines here (I liked #4 & #5  but all are hilarious and true).

Whenever they do talk to you – which is always when it’s convenient for them – they suavely tell you what you want to hear. So if you have weak moments like me, your ego easily gets sucked into their charm. But the truth is: If a guy doesn’t respond to you within a reasonable amount of time, keep and make plans, and show you consistency with is ACTIONS , he’s not respecting you or making you a priority. And I’ve got to believe I’m deserving of someone who is into me and sees my value. If I want someone who is serious about me  – I need to start valuing myself more. And stop giving my contact out to these charming boys with their little black books (which are now called iPhones).

bc31f54e15539496b0320135e3e8656e  fuck boy repellent

My first instinct suspecting what these charmers are up to has always been right, yet I still gave them my number. Why? I think my ego was flattered because who doesn’t like an attractive man who’s charming? The problem is, I’d like someone to, actually I deserve someone to, charm me for a while – not just a month or until I consummate the relationship! I recently decided my continual talking to fuck-boys is a direct reflection of my self worth. If a man doesn’t want to charm me and make plans and respond to me then he simply doesn’t want me. Because a man who wants me would obviously: respond, initiate and show me he cares. I’m finally in a space where I’d rather be single than play games and spend my precious energy and time on flaky boys. At least this is the pep talk me and my girl friends have been giving ourselves lately!

fuck boy stop texting him


Another shocker you single ladies might have run into – married men (who are NOT in an open relationship) will make passes at you. Seriously, WTF?! These are like the ultimate fuck boys. They somehow got married and yet still manage to get their fuck-boy game on. Stay clear ladies! If he cheats on his wife – he’ll cheat on you. If he respects women – like his wife, he wont be making passes at you. End of story. Don’t get sucked into his sappy story of why he’s miserable in his marriage. Not your problem.

dating married men



Then there’s the the friend’s who set you up – blind date kinda thing. This is more of a rarity for me, but my few set ups were like an episode on a reality tv show. The best one was a 30 year old virgin who told me he was saving himself for “the one”. Now there’s something endearing about this, but with my relevant background – being a virgin until my wedding night – I felt strongly that I was put into his life to deliver a very important message: You can date someone for years, adore them, get married and on your wedding night discover you have NO sexual chemistry. At all. Like for real – this is my story which ended in a divorce after a 10-year-long platonic marriage. I do respect the self-control in a virgin, dedication to a belief, and the fact that this type of guy is the opposite of the fuck-boy. But where’s the man in the middle?


Then there’s the nice guy – we call them the “type of guy you marry”. Mostly we girls don’t want them, we want what we can’t have. We’re drawn to those fuck-boys or men who reject us. But why? My theory is because subconsciously, we’ve been programed (due to a long history of heartache, pain and failed relationships) to believe we’re not worthy of a great relationship with a man who sees our value and wants us in return. And if we do find a great one and haven’t worked through our subconscious self-worth issues – we’ll probably sabotage it in one way or another. Which is really a shame. Everyone is worthy of a person who values them!

This is not to say that you should date all “nice” guys and give them a chance. I mean maybe you should give them a few dates to get to know them. But after 3 or 4 dates, you’ll likely have an idea if you are into them or not. If you know in your heart you don’t see a future with them, don’t lead them on and don’t “should” yourself into dating them. Which can be hard if they’re persistent or giving you attention – which we all love!  I have repeatedly allowed men to push their way into my life even though I knew in my heart they weren’t right for me. And I regret that for two reasons. First, that’s selfish and cruel to the man, especially when he leaves his 6 figure job and moves across the country. Yeah, I feel really shitty about that story (to be fair – I did urge him NOT to move). And secondly, you’ll never have these years, months, days or hours back! I cannot get back the long months I’ve stayed in relationships because I was too afraid to be alone. Those days are over and keeping my house the way I want it, sleeping in until I want, and not having to worry about my morning breath is FABULOUS!

I also went through a stage where I told guys – I’m not really looking for anything serious, I’m busy and focused on my kids. And I definitely don’t recommend saying that! You’re basically asking for a man to “hook-up” with. And girl if that’s your game – get it. But be real with yourself when you put that out there. Don’t be bitter when he doesn’t respond to you after he gets what he wants because you just gave him the hall pass by saying, “I’m not looking for anything serious.”

I share all of this because I’ve been evaluating my dating life. I strongly believe we get exactly what we want in life and believe we deserve. So if you’re getting shitty men in your dating life, the question needs to be asked – why? I personally have to own that I been inviting the shit in.

I’ve got to believe that I’m valuable and worthy first – before a confident man will see that in me. Like attracts like. Today, I’m focused on being the person I want to attract.

I listen to this great youtube video by Louise Hay in the mornings and the following affirmations really resonate:

I don’t have to earn love.

I am lovable because I exist.

And others reflect the love I have for myself.

The last line really resonates with me “others reflect the love I have for myself”. When we love ourselves so much, we don’t allow people to walk on us. We demand respect for ourselves. And we’re worth it! So if you see a lot of questionable behaviors from people in your life – ask yourself why are you allowing this?


1.) Don’t get your hopes up with fuck-boys and players. If he walks and talks like a player – he is a player. Avoid him unless you’re interested in just a hook-up because you can’t change people.

2.) Don’t meet up if you’ve never had a phone conversation, regardless of how much you’ve texted. You can tell A LOT via a phone call and save yourself so much time/energy!

3.) Don’t EVER agree to dinner if it’s the first meeting. You could be stuck in the worst 2 hours of your life. IMO it’s always best to go for coffee or a drink for the first date.

4.) Don’t trust a married man who flirts with you. #cheater

5.) Don’t waste your time with non-comital men. If after several dates/months have passed and he doesn’t want to “define” what you are (no matter the reason) – he’s not that into you. It’s okay to be “officially dating” and not unreasonable to get clarity around what your relationship means! 

6.) Do treat people how you want to be treated.

7.) Do pay attention to HOW he makes you feel and WHAT his actions are (not so much what he says he’ll do). And follow your gut! If he makes you feel bitchy, irritated, argumentative, stupid, or negative – move along. You should feel like the best version of your amazing self!

8.) Do get rid of your ridiculous prince charming lists (if you have them like I did) and focus on how a man makes you feel. You should feel valued, adored, cared for and have fun! Be open to the Universe delivering someone that could be greater than your imagination. Sometimes we spend so much time trying to control every detail, we miss out on someone amazing. I’ve been pleasantly surprised by some men.

9.) Do date someone you’re attracted to. If you don’t feel chemistry and sex is important to you – move along. Sometimes I’ll give a guy a couple dates if he’s amazing in a lot of ways but physical appearance, because I have seen attractions grow in past relationships. But girl if after you “Marvin Gaye get it on” and it’s terrible – give yourself permission to move on – we all deserve to have chemistry with our lovers! 

10.) Do be the person you want to attract. Always be yourself – it will come out in time anyway and people could save themselves a lot of time and heartache if they just owned and loved their authentic self!

11.) Do be honest with him. But remember BALANCE – don’t be a stage five clinger – sharing your every thought with him all throughout the day…unless of course he’s pouring out his love for you – then get that romance! 

12.) Don’t text him 10x a day without response or be the one to initiate everything. A great man will have his own life and friends – as should your bad-ass self! And a man who wants you, as you deserve, will initiate communication and plans.

13.) Do be super cautious. One of the first guys I went on a Tinder date with convinced me that he should come inside because he was a contractor and wanted to give me a quote for remodeling my bathroom. To make a very scary story short, I had to call 911 to get him to leave. I have since seen him on different dating apps – 2 years after the incident. I recommend NOT allowing a man in your home if you’re not feeling him – no matter his line. And don’t be naive thinking they don’t have them. Many self-proclaimed players have told me first hand, “You always get inside – whatever the line you have to use.” #assholes. Also, I strongly recommend you tell a very good friend where, when and who you’re meeting. You never know what someone off the internet is really like at first. 

14.) Do follow your gut with people. If you feel off about someone – there’s a reason! That’s your intuition guiding you. Mine has never lead me astray, even when it seemed illogical. 

15.) Do enjoy this colorful journey and be prepared to laugh your ass off.  You may even want to pre-schedule a wine date with your bestie after the dates – you’re definitely going to have stories to share! 

16.) If a guy asks for your Snapchat there’s about a 99% chance he wants you to send him naughty photos.#justsaying And if you’re in your 30s and don’t know what this is – it’s a video/photo sharing app where the content DISAPPEARS #notthattheresanythingwrongwiththat

Lately, after all these exhausting experiences, I’ve had this growing desire to STAY. SINGLE. FOREVER. But I just really like sex and romantic relationships – so nun-life is not the final answer for me! Here’s to reevaluating my dating life – and hoping the long list of things that DID NOT work for me on this journey of dating in my 30s can help you. If you’ve got any tips on how to date in your 30s – pass them along ladies! Heaven knows we single gals need all the help we can get.

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3 thoughts on “How not to date in your 30’s – 16 tips

    • You’re not alone girl! It’s crazy hard sometimes. Something that’s helping and I didn’t write it here is I wrote on my mirror – “I deserve to fall in love”. I read it every day and it has me feeling optimistic!

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