Where Do I Begin with Dating?

Ask Krista


Hi Krista, how would you respond to someone who doesn’t know where to begin with dating? It’s a big, scary world, and there aren’t any manuals on starting at square one.

Oh my gosh, I loved this question so much that I wanted it to be the very first of my new “Ask Krista” series. So many people reach out with dating questions that I decided I need to start featuring the ones that I think might be more common and could help others.

The dating world is so big that it’s hard to figure out where to start and can feel overwhelming. Starting all the way at square one, I’d say you should first give yourself a mini pep talk. Or better yet, I’ll write one out for you.

Dating isn’t very different than any other interpersonal interaction you have with someone on any given day. It’s all about getting to know people on a deeper level and figuring out whether or not they’re someone you want to keep seeing. Don’t overthink it too much. Enjoy putting yourself out there and realize that there are so many people in this world that if a date goes poorly you’re just going to move on to the next person. You are unique and special in your own way, and someone out there is going to absolutely love you for that.

After you’ve given yourself a little push it’s time to figure out where exactly you want to start. There are apps, websites, and networking events that are all dedicated to finding love. It’s difficult to sift through the dozens of options, but it’s definitely not as daunting as it seems. My advice is to start small. Begin with one or two dating techniques. For example, choose two dating apps that seem to be good for you. You could do one swiping app like Bumble that is built for more casual dates, and add one profile app such as OK Cupid. I’d refrain from spending money on a site at least the first few weeks so you can just adjust to how the online dating world works, then you can better navigate the other sites with a little more ease.

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Be yourself online. Don’t worry about being “cool” or impressing your suitors; you’ll have more long-term success in the dating world if you don’t pretend to be someone you’re not. If you aren’t naturally witty or clever, don’t try to come off that way on your profile. One thing I noticed when I was dating was that everyone seemed to love camping and the outdoors. I haven’t been into that since I got sick with POTS, so I actually made a joke about how much I hated hiking and that didn’t know a lot about sports. Guys messaged me and thought my transparency was funny. I also met more people that I actually got along with since I was open about the fact I am not into hooking up, I am a Christian, and I have a natrually silly personality.

When you’re talking to people to go on dates with proceed with confidence and know that you are a great catch. Realize your worth and know that you are doing an amazing thing by putting yourself out there and trying to find love! You are brave, you are a catch, and you are doing your best to find the relationship you are looking for. At the end of the day as long as you are trying you are being productive in your dating life.

Lastly, don’t let the dating world get you down after one — or even a dozen — bad dates. The odds of you meeting someone to settle down with after just a few dates are so incredibly slim. If you really don’t hit it off with someone or do something to embarrass yourself (it happens to the best of us! See hereherehere, and here), just laugh at the situation and move on. You probably won’t have to see your date around again, so don’t even give it another thought!

The more you date the closer you are to finding someone who is right for you. In the meantime you will learn so many different things about yourself and other people. Just keep your heart and mind open, and don’t give up hope. Dating works differently for each individual and sometimes it takes people kissing a lot more frogs to find their Prince Charming than others. You can be excited and think about what you are working towards, but don’t forget to enjoy each day of your life. One day you’ll be married and settled down and might look back on your twenties as being one of the most confusing and lonely times, but you can also make it one of the most adventurous and freeing times of your life. Make the most of your youth while it’s still here, and create fun and beautiful stories to tell your spouse about later when you meet them. Good luck, and remember that persistence pays off.

You Aren’t Responsible for Your Ex’s Happiness

One of the questions I get asked the most is, “How do I stay friends with my ex?” My answer is simple enough to make one word: Don’t. 

Y’all know I’m all about spreading kindness in the world. I strongly believe you should leave every person better than you found them, and one of my favorite quotes from Taylor Swift is,

“No matter what happens in life, be good to people. Being good to people is a wonderful legacy to leave behind.”

This is such a beautiful sentiment and I think making people’s hearts feel warm and fuzzy is such an amazing superpower we all have. One person you absolutely shouldn’t worry about making happy, though, is your ex. Whether you guys dated for 6 months or 6 years, there are very few circumstances where I think it’s healthy to remain friends with an ex once you’ve broken up.

Sometimes people argue that they think remaining friends is the “mature” thing to do, however, I think many often just an excuse to keep tabs on someone you once dated. As an adult it is so important to look out for your own mental health and wellbeing, and it’s rare that people end a relationship and one or both parties isn’t hurt by the breakup.

I’ve never stayed friends with anyone I dated. The way I see it, I already have enough friends, and there isn’t a place in my life for someone who was once romantically involved in my life. Furthermore, it saves the drama that could possibly come up when you find someone new. You don’t have to worry about your ex’s heart hurting, and you don’t have to make the special person in your life feel at all uncomfortable about a past.

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If I saw any of my exes now I wouldn’t have any sort of feelings — negative or positive — about them. Time heals the heart well, and I couldn’t imagine being with anyone in the world other than Robert. Still, though, I don’t have a need for any of my past relationships. I learned the lessons I needed to from each of them, and hopefully anyone who’s gone out with me can say the same with the confidence that I wasn’t the right person for them.

My advice to you if you’re wondering when to reach out to someone you broke up with is to choose to never text them. Choose to move forward in your life, cut ties completely, and to realize that there are bigger and better things ahead of you. Unless this person is absolutely the exception to the rule and you feel like you want to try one last time to make things work, realize that there is someone out there who you won’t have the same problems in the relationship as your ex with. You likely didn’t work for a reasonand there are so many other people in the world that you can now have room to find a person who will work beautifully with you.

Don’t get me wrong, I’m not trying to tell you this will all be so easy. The first few days of a breakup are the hardest because you go from having someone in your every single day life to never talking again. Don’t use the excuse that you need to “be there for” your ex to talk them through your breakup, though. Block their number, delete them on all forms of social media, and cut ties in any way that you need to so that your heart can heal and you can have a new, healthy relationship one day. In the meantime, rely on friends and family to get you through your breakup and realize that your forever person is still out there — it just wasn’t your last boyfriend.

Dating Is A Numbers Game

As unromantic as it sounds, finding your forever and always person is all about giving people chances and dating, dating, dating. One piece of important advice I give to all of my friends is that dating is a numbers game. The more people you go out with, the more people you won’t hit it off with, but the greater chance you have to find the person who is right for you.

Some common complaints I hear about dating are:

  • “Online dating doesn’t work for me. I’ve been on two Match dates and they were both nightmares!” Well, maybe that just isn’t the right site for you, but honestly about 1 in 8 dates are going to likely be duds that won’t even turn into a second date. Sometimes you’ll have more bad dates, sometimes you’ll have a few good ones in a row. Giving up after only a few chances, though, isn’t going to be the attitude that helps you to meet someone great.
  • “I don’t want to tell people we met online. I want our story to be better than just meeting on a dating app!” I don’t get this. At all. Who cares how you meet someone amazing, as long as you do? When Robert and I tell people how we met we start off by saying that we met online, but then we immediately jump into our first date story about how he almost stood me up, then how when we did actually meet that I was more interested in petting a cute dog I found outside the restaurant than greeting him. I love our story so much, and we have so many fun moments to sprinkle into it that “OK Cupid” is only a sentence in the story of how we met.

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  • “There isn’t anyone cute near me. Guys here are lame.” Unless you live in a teeny tiny area, this is an enormous statement for the entirety of the young adult population where you live. First, pictures can be deceiving. I have a few friends who I absolutely know would make great matches, but they’re unwilling to even give someone a chance because of a few Facebook photos. Sometimes attraction can’t be felt over a computer screen, and although I think it’s an incredibly important component of a great romantic relationship, I think giving someone a chance — even just a 1 hour date — could be a game-changer for you. If a friend wants to set you up, give their match a try! After all, there’s a reason you came to mind when they decided to pair you with your date. The very worst-case scenario is that you wasted an hour or two of your entire life on someone you’re never going to see again. Then, if the same friend tries to set you up again you can politely decline if it was really that bad. Having an open mind can be such a great asset to the dating world.
  • “I don’t want to do the casual dating thing; I want an exclusive relationship!” Okay. 99% of the time that’s not going to work. Unless you turn a friendship into a relationship, odds are you’re not just going to meet Mr. Right on the street and realize that the two of you are perfect for each other. You have to be casual at some point in your relationship; you aren’t supposed to know right off the bat whether someone is going to be your new significant other. Sometimes people will tell you that they knew right after meeting someone that they were going to marry them, but that’s a rare miracle in the dating world. You typically become more drawn to someone as you get to know more about their heart and values, and it takes time to really get to the nitty gritty of someone’s true personality. I totally know that dating around is exhausting and can be a chore, but you rarely get beautiful things in life without working hard for them.

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Today’s Lesson: Your dating motto for 2018 should be, “It’s just a date.” Stop overthinking dating and start taking chances on things that scare you, and open up your mind to the possibilities around you. I strongly believe there is more harm to being close-minded than being too picky with who you choose to spend your dates on. Be careful, and be smart, but open up your dating pool to some people you might not typically go out with. Then, watch how your dating life transforms through the lessons people teach you and as others begin to open their hearts up to you.

Fast Five: Pre-Date Jitters

I have been on my fair share of first dates now, and I’ve figured out some pretty good standard practices to make first dates go a lot smoother. Here are a few quick tips to take some of the jitters out of a first date:

  1. Have a few different “date” outfits picked out. For example, when I first started dating in the winter I had two first date outfits I would wear depending on my mood. The first was a gray V-neck sweater with leggings and black heeled ankle boots (Right, Robert?). The second was jeans, brown leather boots, and a ballet pink lacy t-shirt. By having specific clothing as my “go-to” date outfits I never had to worry at the last minute that I didn’t feel good in my clothes. If I feel edgy I’ll switch things around a bit, but it’s nice knowing that I have two killer go-to outfits.

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    Aaand summer calls for swapping out the sweater for a lacy tank! I also always paint my nails different colors — that’s my one beauty must-have.*
  2. Create a “dating playlist” to jam to on your way to the date. Even after dozens of first dates, you still sometimes get a little case of the butterflies before going out. By listening to feel-good songs you can dance around in your car and forget about any of the anticipated awkwardness.
  3. If you’re talking to a couple of people at once, go back and do a quick overview of the conversation you’ve had with your date. It’s obvious people usually have a few options, but is still kind of embarrassing when you mix someone up with another prospect. Something about meeting someone in person for the first time helps you remember details about them, but before that it can be easy to confuse one online date with another.
  4. I like looking over a menu before going to a restaurant if I am concerned about working around my food allergies (I have acquired many the last 2 years — what kind of 25-year-old doesn’t know they’re allergic to tomatoes and potatoes?!). That way I can relax and enjoy the date instead of take twenty minutes to customize an order.
  5. Remember to relax and have fun! The person you are out with agreed to go on a date with you, so there is something there. Even if you just have another notch in your dating belt after, you’ve also gained a new experience and collected another story to tell.

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Do you have any other ideas to make dating a little bit easier? I’d love to hear about it in the comments. 🙂


*Photo taken by my beautiful friend Audrey! Check her out if you are in the DMV and need a photographer for anything.