Three Things I Wish I Knew Before I Started Dating

It’s no secret – my dating journey has been…well…a bit of a bumpy road.

One thing that they don’t tell you about recovering from anorexia – or any eating disorder for that matter – is that sure, you may put on the weight, but that the mental recovery — and shutting off the negative mental tapes that chiseled away at your heart for years and years…that recovery is the most difficult. Because it seeps into every aspect of your life — including dating.

And so, hence, why I’m just now starting to go on dates and open up my heart in the hopes to let someone else in.

But here’s the thing…I think I had built up the idea of dating so much in my mind, that I wish I could go back and have a sit down, face to face real talk session with my old self. And when I say self, I mean…my 4 months younger self haha

And just spoiler alert — I’m going to want to hear your thoughts on the matter too 🙂

OK – The Top Three Things I Wish I Would Have Known Before I Started Dating

Don’t try to be who you think the other person wants you to be.

This may seem like the biggest “duh” in the world. But it goes back to my perfectionism — the gal’dang beast that led to my anorexia in the first place. Being perfect is not what constitutes you as “eligible” for dating. Care: just be yourself.

Because you need to know if who you really are “works” with who they really are. And if you’re just going to try to be exactly what you think they want, not only is it going to be incredibly exhausting, but also – you’re doing the potential relationship a disservice with inauthenticity. It’s such a buzz word, but really just be authentically you.

And that means talking about things that mean a lot to you. Talk about faith. Talk about important issues. But what’s more than talking, is listening. Because just as important as sharing your own thoughts, is learning theirs on the things that matter to you.

But at the end of the day: you’re enough, you’re beautiful, and you’re worth being loved.

Makeup is great, but guys aren’t falling for a perfect eyeliner application and snatched highlighter.

Ok – this one was really hard for me. Because again, that damn eating disorder plants these lies that really screw with your head. But I was — and am trying to work on — I was always that girl that…if I was going to see a guy, I would have to look perfect. Full face of makeup as though I hired a glam squad. Not a hair out of place, and dang it, I was going to look like I could be on the cover of a gosh darn magazine.

But you know what? Makeup doesn’t make you worthy of love. Makeup doesn’t enhance who you are as a person. It doesn’t make you more attractive or more beautiful. Sure, it’s fun, and if you enjoy it – awesome! Go for it. But know that who you are with and without makeup — she is worthy of the same amount of love.

And what’s more: guys — at least the right ones — actually prefer women without all the make up. Which, now that I’m thinking about it makes a lot of sense.

Believe it or not — this makeup obsessed girl has now switched to tinted moisturizer, chapstick and ONE coat of mascara. (Not three!)

Eat like a lady.

Ok – this is really not what it sounds like. Because I’m sure as heck not talking about ordering a salad. I’m talking about — actually, my eating “form” — as in — Care, DON’T MISS YOUR MOUTH. I mean, I live in a studio, I eat most of my meals in the privacy of my home with just me and my YouTube videos, and so I can sometimes forget how to like…I don’t know — chew? Practice bare minimum manners? Yeah — gotta work on that.

Dating is really fun!

Finally, this one is the biggie. Dating is fun. Period. It turns out that being vulnerable and letting someone in to see the real you is not only incredibly affirming, but it’s just an awesome feeling.

Not to mention, you’re opening yourself up to so many new adventures. There’s a reason why there’s a booming industry around “date spots” — because they’re genuinely FUN to experience. And with someone you enjoy getting to know…it’s shocking, I know…but it’s a great time.

SO there we go, I know I added a fourth, but I just felt moved by the spirit.

I would love to learn YOUR top dating advice. Because I am always eager to learn, and I’m finding that the more dates I go on, this list gets longer and longer.

Have a happy memorial day! And I’ll talk to you on Wednesday!

Unless, of course, you’re on Patreon, and in that case, your video will be uploaded tonight!!

“This is what the Lord says to these bones: I will make breath enter you, and you will come to life.” Ez 37:5

Comes in other fun colors too!


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264 thoughts on “Three Things I Wish I Knew Before I Started Dating

  1. Lol… You’re cute! Be yourself and like who you are. Be honest with yourself and your date. Never settle. If you don’t like something, you don’t have to put up with it. And you look great and you’re a sweet girl. Anyone would be extremely blessed to be in your company.!

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    1. Thank you so much Tony! never settle — that’s a great point too! gosh, what a kind thing to say — thank you again! have a great week! hugs xo

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  2. Hi Caralyn, I think you’re doing great. I was pumped when I read your tip about using minimal makeup. It’s so liberating, isn’t it? I used to wear a decent amount of makeup but my husband kept encouraging me to just forget it. He really boosted my confidence and now I hardly wear any! So I agree with you 100% there… the good guys don’t care about makeup. Keep enjoying the dates and trusting in Jesus! That is the most important thing and you are very faithfully doing that. 🙂

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    1. Hi Hannah! Oh gosh thank you so much! 🙂 It really IS so liberating!! And thank you — you’re absolutely right — having Jesus be part of the process is a MUST! have a great week! hugs xo

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  3. It sounds like you have already worked out what it took me years of marriage to discover – be yourself and don’t try to be who you think they want you to be. This is so so important. The right person will love you and value you for exactly the awesome person that you are. Keep being real.

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    1. Thank you so much 🙂 yeah – I’ve received so much great advice through this blog! And gosh – thank YOU for that awesome advice and encouragement. means a lot! big hugs xo

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  4. Back in the stone age when I was dating it was so different than today. These were times when all roles were being question and many young women started being more aggressive in meeting their needs. Being raised in a household that getting married was not the ultimate goal by my mid 30’s I really was ok with that. Then I answered an ad in a christian singles paper ( long before eharmony) and that changed my life in ways I could have never expected. That was over 22 years ago and now that woman I am leading to her final resting place with the Lord God Almighty!

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    1. Hey friend! yeah dating is so weird now a days. thank you for sharing your love story – it sounds like a really beautiful relationship. Sending so much love and hugs xo

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    1. Thank you so much! I can’t wait to read it! And gosh, thank you for your prayers – it means so so much!!! 🙂 big hugs xox

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  5. My dating life is less than lucrative, and I’m okay with that. I’m working on myself right now, and I’ve finally accepted that I’m where I need to be. I’m glad I don’t have anyone else to take care of (except my pup Harper)!

    That said, I also have some dating tips:

    1. Don’t settle.
    2. Listen to your gut.
    3. Say adios to men who use shame, even if they are “just joking.”
    4. Don’t try to rescue someone. Pity is a horrible base for a relationship.
    5. Find someone who is okay with being alone and also who can handle you doing your own thing. It isn’t even healthy for married couples to be constantly joined at the hip. Date someone who respects that your world does not revolve around him and y’all’s relationship.

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    1. That’s such great advice – don’t try to rescue someone. On that same token — the idea of “missionary dating” — or dating someone with the hopes that they’ll convert to your faith eventually…I don’t think that’s wise either. Thanks for sharing your wisdom! big hugs xo

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      1. I agree. That’s a rocky hill to climb, and your own morals/values/beliefs could be lost/sacrificed. I’m not a huge fan of the idea of casual dating. I’m sure it works for some people, though! I just know myself and how easily I get attached to people, and I don’t think it’s smart for me to do it.

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  6. The hardest part of dating for marriage is that you often don’t know, while you date, what the other person is like when you aren’t dating them. There’s always that context that interferes (to greater or lesser degrees) with knowing who the person is when their guard is down, when they’re panicking, when they’re angry, when they are all the things they want to hide or change about themselves. That’s more than willing vulnerability; I speak my heart when I say that this moments are the scariest for me because I don’t know if my wife can live with what she sees, and if she can, if she can forgive me for it. Those, though, are the moments that make a lasting relationship, if both sides are dedicated to making changes and allowances for each other. Like I’ve taken to saying, “if you ‘like her, but…’, you only like her butt. You have to love even the ugly parts to deserve the beautiful ones.”

    Good luck with your search, and God’s blessings.

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    1. That’s a really great point. That’s what’s so beautiful about dating someone from your home town or that you knew growing up – because you know their character, their family, their values. Thank you for sharing your story. It sounds like you two have a beautiful marriage. 🙂 Hugs and love xox

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  7. But at the end of the day: you’re enough, you’re beautiful, and you’re worth being loved…Love this! ♥️

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    1. Aw thank you Terese. The dating world is definitely an interesting one to navigate! Glad you stopped by! Hugs and love xox

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  8. Rule #1: There are no rules!

    But in all seriousness, authenticity is probably one of the most important aspects of meeting someone new. It can understandably be difficult because we want to put our best foot forward, especially when we’re working on building up our confidence again. Thanks for sharing!

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    1. Hi Tammy!! You’re so right about that – growing and learning. It’s the best way to be! I appreciate you stopping by! Hugs and love xox

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  9. Like others have said, just be yourself. Not always easy, but it makes it much more efficient for finding the right person. Being happily married, I’m very thankful to have found someone (the one person, actually) who I can truly be myself around. It is so worth it to wait for the right person. You are a beautiful woman, inside and outside, and you will definitely find the one for you! 🙂

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    1. Thanks so much – that’s really such great advice. Thanks for sharing that – it sounds like you have a wonderful marriage! I appreciate that! 🙂 Hugs and love xox

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  10. Just. Be. You. Be open. Be accepting, but don’t be disrespected! All dating is is interaction. Revealing of character. Any guy who gets to know you and your story from you is a lucky, lucky fella.

    Trust your instincts. Follow your heart!

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    1. Just be you – that’s such great advice. Interaction. Revealing character — i love that so much. thank you Eli! hugs xo

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  11. I was always too shy and had to go through some stuff… which I now see is God’s protection so I never was a dater. I never understood casual dating as I’ve always prayed there would only ever be 1 for me. While i never “dated” God had me in customer service for 5 years now… wow… and I have learned and been so refined so much by meeting all kinds of different people. I also get attached easily so guarding my heart was obvious. This has been the best situation for me. But, with that said, God sent 3 people (guys) in my life to really have me pay attention to who I am and as lessons and I have learned and grown so much. He knows exactly how to get to you.
    1. Reckless
    2. Perfect test for me
    3. An atheist but he was there for a reason and taught me so much … a lot being let people go and you cannot open a blind person’s eyes. If they choose to be blind let them go. Do not cast your pearls before swine … no matter how perfect you are for each other.

    So I do not “date” and am finally content with being single and can enjoy it. Nobody in the Bible ever stressed about finding a spouse. God always had them meet at the time they were supposed to.

    He who finds a wife finds a good thing … and she is to be hidden in Christ.

    He is to ‘find’ a wife. A wife does not search or chase. I’ve been studying biblical marriage and it’s so opposite of what the world teaches us to do. God’s metaphor is so beautiful because He is the perfect Husband and we are His bride he has chosen and he is coming to get us.

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    1. Thank you so much for sharing your story. There’s a lot of wisdom there – God’s timing is absolutely everything. And we can just trust and have peace in the waiting! hugs xo

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  12. Just be yourself and the right one will appreciate you for who you are! In the beginning meet at your destination and don’t allow the guy to pick you up at your place. Better safe than sorry. Have fun!

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    1. Thank you so much Lane!! That is really such great advice — better safe than sorry for sure!!! big hugs xox

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  13. I really enjoyed reading this article. My top dating advise is to take your time on the journey and do not waste time on people who are not worth your time. Sometimes we try to make people fit into our lives who are not part of our journey. Thank you for your transparency.

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    1. Thank you so much Ada! I’m so glad you enjoyed the read! Take your time on the journey — I love that so much! And you’re so right — it’s funny, i really needed to read that today about not trying to fit people into our lives who are not part of our journey. That can be such tough advice to follow, but you’re absolutely right. thanks for stopping by. big hugs xo

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  14. Hi, Caralyn-
    As someone who lived alone for several years before marriage: the possibility of sharing your whole life — your daily life like what to have for meals, where to live, what will this person think about this topic, or my viewpoints. My wife and I were friends hanging in the same social group for over a year so by the time we decided to date we had a knowledge and trust in each other. A very good thing. . .

    This is a guy you should let know about this website (if you are wondering). Whether through an offhand comment, where he takes his own initiative and peruses around the postings on his own(and is genuinely flabbergasted at the breadth of this blog), or a more direct “discourse” probably would not matter much. This blog is a main part of your life and this guy should see this side of you.
    In Him,
    Jeff

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    1. Thank you so much for this awesome advice, Jeff. You’re so right about that – having that foundation of friendship is so beautiful and so important. And you’re right about the blog. It is something that I definitely will share with someone I’m serious with — maybe not on the first date — but it is such a huge part of my story, and I am looking forward to being vulnerable enough with a guy to share that. I really appreciate you encouraging me on that, because to be honest, it really is something that terrifies me. That I’ll be “found out” before I’m ready for him to know ALL that this blog covers. I mean – yikes. haha. But you’re right – it’s important to let him into that too. You’ve really blessed me with this comment tonight. thank you. and also – it sounds like you and your wife have a really beautiful marriage — gives me hope!!! 🙂 hugs x

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  15. Two good books to take a look at if you haven’t read them yet- “How to Get a Date Worth Keeping” by Dr. Henry Cloud and “Boundaries in Dating” by Cloud & Townsend. Not necessary to read both, I have a slight preference for the first one. They offer great practical advice for navigating dating and relationships and managing expectations. Love your posts-they are fun, sassy with tidbits of wisdom. Keep ’em coming! 🙂

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    1. thank you so much Alison for the great book reccommendations!! I will definitely have to check them out. I am always on the hunt for a good book or audiobook! and these in particular sound right up my alley. And thanks for your . kind words about my posts!! means the world 🙂 hugs and love xox

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  16. Haha! Love your three tips. The makeup one was a no brainer for me — I hate wearing makeup! Took years before someone could trust that I’d try out moisturizer (my boyfriend’s sister “sneaks in” chapstick on Christmases, that’s adorable of her). The first is hard because of …issues involving trust. Whee. Third, LOL. Snacking on a coconut cake slice and I’m laughing quite hard.

    Okay, you asked readers to contribute. I don’t find rules in dating useful, so I’ll do a “three things I wish I knew” too. 😀

    1. Future husband can show up in ways you don’t expect. He could come with Incredibly Bad Timing — God has His humour, and I can laugh now, too. And he might not look anything like what you imagine, fantasize, dream up, etc. You could have no idea. God can be funny like that. Furthermore, don’t give up on a guy too quickly. You’re getting to learn him, and he’s getting to understand you. Sometimes he’s got stuff to work through — you’re not always a reason for it — and he may need space and time to deliberate. Same with you. Can you get through the bumps, the unexpected scares and undesirable bits you didn’t think could come? Can you two work together, can you two go on a limb for the other if needed, can you lean in and out as you’re figuring out how on Earth do two people entrust God with making a shared life with two unique individuals who are His children?
    2. Don’t talk about the dating partner -> boyfriend to others whom you KNOW to have problems with you. Not worth it. Not worth those tears and brokenness at all. It will hurt your relationship. So-called “friends/family” come and go, but if future husband is supposed to be future husband, prioritize building up life with him. He could be in this for the longest haul with you. Do you want your marriage to begin with regret and hatred from such pettiness? If he struggles with similar experiences, can you hold each other up and through some dark, dark days and nights? Sometimes you must choose your husband over your gals, and that’s a good skill to learn before things go into engagement zone. He has to learn that skill, too. And it could play out different for both of you.

    3. Don’t make previous attempts or exes a foundation in your budding relationship. It’s good and recommended to be aware of things that went wrong before, but a guy isn’t a toy to replace unhappiness or trauma. You know who to talk to for life repair? God. Dial up your patron saint for assistance. And seek out help if you need it. You got a chance for a new direction, a different future outlook. Baggage needs to be sorted and unpacked, but for the love of the future spouse, he’s not there to fix you. Nor you to fix him. Again, you got God’s calling card. Remind him he’s got one, too. Better yet, make some mutual chats between you and your Daddy, and invite potential future hubby to that party.

    Coming up to three years together in July, and I gotta remind myself of these at times. It’s not always tips to tell my younger self. Hindsight has this funny characteristic of being relevant in the future. 🙂

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  17. It’s fun following your life path. You are rediscovering the most important things and that is being yourself and being comfortable in your own skin. That sounds so duh but is actually something very few people ever accomplish. What is make up, clothing, cars, houses, jewelry, etc? but things to make the outside look good – but the inside may still be ugly and damaged. Only a guy who also wants what is inside of you and just as importantly inside of himself is worthy of your time and attention. It’s hard to find a guy like that today, or a girl for that matter. But you ARE a girl like that so only settle for a guy worthy of you. My advice about dating is pray-pray-pray and then pray some more. Ask God to guide you to the perfect guy for you – the one he chose for you to be with. I still believe in the lost rib and all of that. That aside I’m glad that you are healing and that you are having fun in your recovery. God bless.

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    1. Oh you’re so kind to say that. Thank you so much for this powerful advice – you’re so right – it’s the inside that matters. And YES! PRAY!! That’s the. EST advice!! Hugs and love xox

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  18. You can’t date everyone. If you do it right, you don’t have too. People do date titles, I get handed business cards. 🙄 Which makes, it weird. I’ve reached the age where if everyone made the right choices they should have business cards to promote that fact. Cool. 😂 Love, has gravity it connects two bodies. God, did it.

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      1. You’re in a weird spot. Being a part of the market that pretty much sets the behaviors that everyone copies.

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      2. Oscar Wilde, was in a similar situation for most of his life. Everything, is material. Not so materialistic, just story material.

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      3. That’s all I have, interesting thoughts. Before the internet, we had to remember things.

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      4. If not, well his loss. We may not agree on, anything. 😂 I wouldn’t wish mistreatment on you. You’re writing has, improved.

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      5. Dating, to marry gave us “shèng nǚ” in Chinese. Meaning the leftovers. There’s a similar name in Japan, I think it’s “dumplings” or, “Christmas Cake.” クリスマスケーキ. Just, dating has given these challenges for women, everywhere.

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      6. Kiss frogs. 😂 I think the upper classes have the same men. High school quarterback types too much time spent over achieving. 😂

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      7. The inner conflict tho. Your need to be liked? Your. Actually being, attractive. Would make men, less genuine don’t you think? Like, it would take a few months of dating to see past everything. To get to here, talking across the table. We’ve talked for a few years, I think. This, is what most people want to achieve when looking for someone. Just, talking across the table. 😂👍 Too bad, I dislike Manhattan. Its up there with dentist visits and TSA.

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      8. I’ve never just, been there for fun. Working or, volunteering. I’ve always wanted an NYPL card. They have, huge sections of books I like to read. I’m, different. I enjoy the higher quality goods of the upper classes but would be just as happy with day old donuts.

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      9. Sometimes. Doors shut because they don’t see you. Maybe. Not you. I’ll be okay. You’re, gonna be okay. That, makes me happy. I’ll take care of my mom and play in the desert. I’ll be, alright.

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  19. I always hated dating because it seemed like the two of us were putting on our best faces…like a performance. I would recommend biking, hiking, etc., with a group of church friends (male & female). While you are naturally real with your friends, God may choose to take one of those friends of yours, and surprise you with more. That’s how it worked for me. It was a heart thing instead of attractiveness-based.

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    1. Thanks so much! Oh wow 15 years! That is really something to celebrate!! 💛💛💛Hugs and love xox

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  20. I love this honest post. My dating advice from someone whose been divorced is to be honest. I’ve been completely honest with everything, including my feelings. And don’t let the fear of losing them stop you from being yourself.

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    1. thank you friend – that’s such great advice — honesty above all else!! 🙂 big hugs to you xo

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    1. thanks so much! i think you’re absolutely right about that — it’s the MOST important! hugs xo

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  21. I did enjoy reading this post. It was interesting to see the transformation in your thoughts from just a few months. I look forward to hearing more of your dating thoughts and maybe even your journey if you are willing to share x

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    1. Thanks so much Rexina! I appreciate that! Yeah it’s been quite the journey these past few years! Hugs and love xox

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  22. I’m just started to learn about dating in recovery, as well. I’m an alcoholic and am so grateful that I can say I’m sober today.
    I’ve got two divorces in my past and was dumped by my most recent ex 5 1/2 months into sobriety after a 4 1/2 year up and down relationship. Today, a year + after we broke up, I know he was not a healthy partner for me, but dang it! Dating without social lubricant is difficult.
    Honestly, I haven’t even really tried aside from opening a Match account because even tho I’ve been in a relationship with someone since I was 16 (add 20 to that for my current age), I really have no idea what I’m doing. 😛 So I’ve decided, for now, to continue my journey of self-discovery. It’s probably better if I finally learn who I am before introducing myself as a potential partner to anyone else.
    Love this post! 💖

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    1. Thanks so much for sharing your story. I’m so sorry that you’ve had to go through that. But I’m so glad that you’ve discovered what you deserve in the process. Yes! Continue that journey! You’re worth the absolute best! big big hugs to you monica!! xoxo

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  23. I really think that you hit the nail with being yourself. Honesty is vital, in my opinion. Also, you want to be liked for who you really are, and know that the other person isn’t being fake, either.

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    1. Thank you Rebel – I appreciate that. And so true – that’s that give and take balance that is so key! hugs xo

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