dating tips from yours truly.

Sometimes I find myself feeling like Charlotte in Sex and the City: “I’ve been dating since I was fifteen! I’m exhausted. Where is he?”

But the truth is… I’ve only been dating since I was 25. I was a late bloomer. I blame home schooling and my thirst for adventure. Back in the day I wasn’t interested in husbands. I was interested in planes, trains and automobiles… anything that could take me somewhere new.

25 rolled around and suddenly I was like I FEEL SO ALONE and all I wanted was someone to sit next to me on those plane rides so I could rest my head on his shoulder. (Turns out strangers aren’t too keen on that.)

At that age, I was under the impression my husband would fall into my lap. I was finally ready, so he could go ahead and ride up on that white horse in all his glory.


am i right??

Newsflash: husband did not fall in my lap. This actually surprised me.

I discovered I had to succumb to that thing most other people do… aka dating.

I wasn’t very good at it, to say the least. I freaked out and took a shot of vodka minutes before one guy picked me up. During that date I pulled a Cameron Diaz (circa The Holiday) and said something along the lines of, “Don’t worry, I’m not going to fall in love with you anytime soon…” I wanted to let him know I wasn’t clingy and obsessive. On the contrary, I was uptight and closed off.

It took more than two months of talking/dating/whatever it really was before I let another guy hold my hand. When he asked about kissing, I said I wasn’t ready.

In general, I put waaaaaaay too much pressure on trying to figure out if this guy or that was “the one” over appetizers.

My mentor told me I needed to make out with the first guy I mentioned. I practically spit out the water I was drinking when she said that. “Aren’t you supposed to tell me to not do that?” I said, bewildered.

I never made out with that guy.

We didn’t end up together.

But now, a few years later, I know what my mentor was saying. She was telling me to calm down and chill out about dating. To not make it as big of a deal as I was making it. To jump in and have fun and see where it goes.

I get it now. During that season of dating I was still struggling to accept the idea that the first person I dated… or even the second… might not necessarily be the person I’d spend the rest of my life with. My sister married the first man she seriously dated, so I figured the same would happen for me.

I was so cute back then.

All this to say, I’ve learned a thing or two about dating over the years. And now I want to share my nuggets with anyone who might need a little help in this area.

Without further ado…

The Six Commandments of Dating.


1) A date is just a date (don’t overanalyze.)

Marriage is a big deal, dating is not. I’m going to say it again… marriage is a big deal, dating is not.

When you get married it’s for the rest of your life, when you go on a first date all you’re trying to figure out is if you want to go on a second one. And after the second one, do you want to go out on a third?

I recently told my guy friend he should ask this one girl out. “But I don’t know if I like her,” he said. “That’s the whole point,” I replied. “To find out if you like her.”

I know a lot of people who won’t go on a date unless they are certain they like the other person first. I think it should be the other way around – go on a date and then determine whether or not you like that person.

Sure, there should be some level of interest and attraction up front, but beyond that I think people should just go for it.

Here’s a great way for guys to ask girls out: “Hey, I’ve seen you around and you seem pretty cool. I’d love to take you on a date and see if there’s anything there. What do you think?”

It’s casual, it’s cool. It lets the girl know it’s not a big deal. It’s just a date.

Also, if there’s a kiss at the end of the first date, it doesn’t mean the marriage is consummated. I NEVER thought I was someone who would kiss at the end of a first date, but then I did. It was simple, it was sweet. I would do it again.

2) Don’t wait around (put yourself out there.)

Get online, go on a blind date, ask someone to set you up. Don’t just sit around in a dark corner waiting for something to happen (…and then complain about being single.)

Coffee Meets Bagel, people. My roommate Greg is madly in love with a girl from it. One of my friends is in a serious relationship with someone she met through it. My friend’s sister is getting married because of it.

Online dating is cultural. It’s not a bad thing. Embrace it.

God cares more about the person we marry than the way we meet them.

A friend from college started this dating challenge a few months ago. After years of not putting herself out there, she’s practically starring in her own chick flick.

Putting yourself out there means you’ll probably get rejected more. But rejection isn’t such a bad thing, I’ve come to learn. Rejection makes you stronger. And when you’re stronger you’re more attractive. Win-win, right?

3) Clarify (aka guard your own dang heart.)

One time I realllllly liked this one guy, and I thought he liked me too. But he was traveling. So I waited. When he finally came back I found out he was kissing another girl… I was crushed.

So now, when I like a guy and I wonder if he might like me too… I ask. Point blank. My results so far: 2 times no, 1 time yes.

Even though it hurt when those two guys said no, it was also a huge relief. I didn’t have to wonder or wait around anymore. I knew the truth. And the truth will set you freeee.

The one time the guy said yes? Bliss.

4) Communicate (all day, e’ery day.) 

Games are for kids. Communication is sexy.

As you date, let the other person know where you are / how you feel – even if it’s scary.
Men can handle it. Women can handle it. It’s respectful, it’s honoring, it’s mature.

I ALWAYS tell people I date: “I don’t want either of us to be surprised where this ends up.” Aka no one is going to feel like the rug was ripped out if this doesn’t work out.

Sometimes this means having uncomfortable conversations that make me squirm in my seat. But I do it because I value the other person, and they deserve to know what I’m thinking/how I’m feeling along the way.

5) Be who you are (small bladder and all.)

I’ve learned to be up front about who I am and what my quirks are instead of trying to pretend I’m cooler than I actually am. “I pee a lot. Like, a lot.” I’ll tell a guy on a first date. “And I’ll always say yes to dessert.” Always.

When I was younger and someone I liked asked, “Do you like this obscure band or book?” I would respond with, “uhhhh yeah, duh.”

I’m so over that now. Aint no body got time for that. Either someone likes me, or they don’t.

6) Allow yourself to be surprised (give people a chance.)

The other night in the kitchen some of my guy friends were SHOCKED at who I said I would go on a date with…

This goes back to the first point: a date is just a date! I wasn’t saying I liked those guys romantically, I was just saying I’d give it a chance.

I’ve learned to throw away “the list” and embrace someone I might not expect. This doesn’t mean I lower my standards. I have high standards. But I’m not picky.

Being picky is not dating someone because of their clothes, their quirks, their hair color, their height. 

As a wise woman in my life once said, “You can change a person’s clothes, but you can’t change their character.” (Thanks, Rozy.)

When people ask what my type is, I can’t really respond because I let that go. Sure, it used to be a flannel-wearing, bearded musician who liked camping and classic literature.

But, in a way… that’s me (minus the beard.) I wanted to date myself.

There’s a great line from 500 Days of Summer that says,“Just because she likes the same bizzaro crap you do doesn’t mean she’s your soul mate.”

Yup. Preach. I know some great couples who ended up together because they let themselves be surprised.

(Also…Married at First Sight, anyone?)


I’ve gone from being a girl who hated dating to one who embraces it. And while I still may be single, I have more hope than ever.

I’d love to hear any dating tips you’ve picked up over the years! Or at least a dating horror story (unfortunately, I don’t really have one of those…yet.)

In the meantime, go get yo’self a date!!



About Hope Naomi

Lover of all things tea and travel.
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9 Responses to dating tips from yours truly.

  1. Love it! Thanks for linking my adventure 🙂 Also everything you wrote is EXACTLY what I have learned as well, I agree with every word- except maybe kissing after a first date-still trying to not let that freak me out 🙂

    • Hope Naomi says:

      It’s been fun to follow your journey over the last few months! I love the life you are living for yourself and the example you are setting for other people. Also… the end of the first date kiss isn’t everyone’s cup of tea 🙂

  2. tempowriter says:

    Would it be concerning for you if a boyfriend your dating ever finds your blog?!!

  3. alysseay says:

    I always love some hope wisdom. Thanks for sharing:). I’ll take the advice!

  4. Being Shayna says:

    This makes me want to date againnnnnn. The awkward beginning stuff is what we still talk and laugh about now. Embrace the awkward.

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