Taking the Online Dating Plunge is Scary

Author: Nicole Chininis, The Dating Game

If you’re anything like me, your experience with dating (or lack thereof) has not been the easiest thing in the world. So much so, that people around me started to get nervous.

“Are you trying hard enough?”

“You know, all it takes is to say yes to a date.”

“Are you meeting people?”

And the inevitable…


I’ve been asked that question more times than I can count. Honestly, I know people never meant it in a negative way, but like, duh, of course I have considered online dating and apps. Who on God’s green earth hasn’t either heard of online dating or tried it? I understand people’s concern, but there were a couple reasons why I was hesitant about it until recently. 

I wasn’t ready
Up until about a year ago, I wasn’t ready to put myself out there like that. I have been burned by the dating world in dramatic and tremendously hurtful ways. That proverbial rug had been ripped from underneath me too many times right when I had made my heart ready and open to someone. The thought of freely putting my heart on the market to potentially get ripped apart did not seem appealing. I was scared and I wasn’t ready.

I knew of no success
Yes, my friends were telling me all of these stories of people they knew who had met people online, but I had not personally known anyone to have a successful relationship due to online dating and apps. I didn’t trust the process. I had no confirmation. And I had nothing positive to entice me to want to join the online dating world.  

I wanted a real life meet
I think the idea of being able to potentially just meet someone by chance in real life made it seem less scary, and I would be able to read them a little bit more. Obviously, that was not necessarily the case because I had never successfully done that, as evidenced by my experiences. I never judged anyone for doing online dating or for meeting someone that way. I never really understood why people lied if they met their partner online and said that they met in the grocery store (seriously, what is that?) However, I couldn’t let go of this idea of the real life “meet cute.” I just wasn’t ready to give that up. 

I’m stubborn
If people tell me to do something, I most likely won’t want to do it. Even if they mean well, I really just have to come into things on my own most of the time. I truly value people’s opinions and I like to talk things through if I’m having an issue, but the more that people asked me if I wanted to do online, the more I did not want to do it. What did they know anyway? I was tired of talking about it and tired of people pushing me to do something I wasn’t interested in. Everyone just didn’t understand.

When I joined, I kept it from everyone
I got to a point when I decided to just dip my toes in, see what was out there. It felt great to get there on my own. I didn’t tell anyone though, because I thought that if people knew I would get even more pressure from people to tell them what was going on, or who knows. By keeping it to myself, I wasn’t setting any expectations for myself or for others, and I could stop at any point if I was uncomfortable. I did something very non-committal and downloaded an app instead of diving right into Match.com, and it was a great decision.

And of course, I learned from all of this
I learned a lot about myself. Primarily, I learned what it meant to do something for myself. I generally am open and truly willing to go out of my way to do things for other people. You need help moving? I’m your girl. You need to talk about something? I’m here for you. You need someone to pick you up? I’m so happy to do so. I love helping and caring for others, but with something like this I needed to do it on my own time. I realized, even though the pain of my experiences hasn’t gone away, what it felt like to have my heart open for experiences.


Baby steps can feel like climbing a mountain. Some people believe that online dating may not be a big deal because everyone is doing it, for others that’s not the case. While you may value encouragement, until you feel ready to take the plunge — keep on climbing that mountain on your own time.

What Not to Do on a Blind Date 

Author: Mary Grace Donaldson, The Dating Game

I went on a blind date, and I thought it was doomed to failure from the beginning. It was set up by a friend of my mother’s, which is an idea I’m just all-around opposed to. I don’t like the thought of being pressured into a dating-type scenario; I want the date to be my idea.

He texted me probably a week prior. We had some good text conversations and some meaningless, dull text conversations — at least from my point of view. After all, he was a CPA… and I had no idea what a CPA and a candidate for a Master’s degree in communications with an interest in community theatre would have in common. Since he went to church, as do I, my mother thought it was a logical fit. But even via text message, I need to feel as though the conversation has… meaning and depth, and I didn’t.

I showed up for our date, which was at a very touristy Italian restaurant in Manhattan, about an hour late thanks to unreliable New York transit. I was anxious at best and I donned a black sequined dress. There’s the first lesson: never wear a black sequined strapless dress to a blind date, or to any first date! When my date realized who I was and gave my dress the once-over, I’m reasonably sure his eyes came out of his head. And not in a good way. More like in a “deer in the headlights” way.

The rest of the evening was filled with more of my eccentric behavior and overt feminism. I talked about my theatre company, my general distaste for all things mathematical (to a CPA, because that makes sense) and, as I don’t believe in the convention of the man automatically picking up the tab on any date, I’m reasonably sure I embarrassed him when I fought with him over the bill. Yes, I took it so far that he partially consented and I took care of the tip.

Where did I go wrong here? Well, it could be asked, where didn’t I go wrong, but we’ll break it down. The poor guy clearly had no interest in theatre, he only does math for a living and he was old-fashioned, so I’m sure he felt uncomfortable with my insistence on taking some of the bill.

To make matters worse, he had been dealing with a family emergency during the day and was nice enough to come anyway. I’d let him talk about the situation but couldn’t cope with awkward silences when he just didn’t feel like talking anymore. I don’t remember much of what I talked about, but the conversation was pretty one-sided.

Now I don’t know if it would have worked out had the date taken a different turn (i.e. if we were actually compatible). Regardless, let’s recap what not to do should you find yourself on a blind date.

  • Don’t wear something that looks overly ostentatious or is trying to make a statement, especially when you don’t know what that statement is.
  • Don’t show up an hour late. If this situation looks like it could be a possibility, try to plan ahead to avoid it.
  • Don’t make awkward conversation that’s only about you and your life.
  • At the same time, don’t try too hard to appear overly invested in the other person’s interests – only to follow-up with how much said interests bore you.
  • Don’t get overly political.
  • Don’t embarrass your date when your date wants to do something nice for you.
  • Don’t try to overcompensate for awkward silences.

Blind dates are uncomfortable to begin with. Hopefully with these tips, you’ll have some better luck than I did.