Well, I suppose it’s time to start writing. After multiple challenging years of dating my 30s, I will share my experiences with you. Sometimes dating can be fun. You meet new people, make new friends, and try new restaurants. But usually, it’s a bit messy.

And, online dating doesn’t seem to make it any easier. On one hand, it should provide you with more options than you’d otherwise have. In reality, it can often give daters an outlet to create an alter ego. It can give them a place to ask outright for a relationship based only on sex. It can allow them to hide their significant other or marriage or children or whatever else they’d rather you not know.

I’ve always been a believer in waiting until your 30s to get married, but after the past few years, I don’t know if I’d wish this experience on an enemy. It can be a painful, long, difficult process… even for the best of us. One friend put it well when he said, “dating in my 30s was one of the strangest times in my life. I was dating people who were 23 to 45. The younger people had no idea what they were doing. The older people had so much baggage. It’s a hard time to date.”

Just last night is a perfect example of how strange things can get. A male friend invited me to a party. He mentioned that there might be a doctor there who I’d be interested in me. Two things seemed odd. First, I thought this friend had been interested in me, so it was strange he’d be the one to set me up. Second, he seemed to think I was looking for a doctor. “What exactly does that say about me?”, I wondered…

Upon second thought, I decided to brush it off and go to the party. After all, it would be good to see my friend. It’s also nice when someone thinks enough of you to introduce you to someone else they think a lot of. And, all doctors are probably introduced as, “he’s a doctor!” to everyone.

Upon arriving at the party, I realized that I hadn’t really entered a party. It felt like more of a setup. It was four people: a couple, my friend, and the doctor. The moment I walked in, I recognized the doctor from somewhere. Everyone stood around asking me question after question about myself for the first half hour. Clearly, I’d been invited just for the setup and everybody knew it.

While we talked, I thought about how I knew the doctor. We met on Match.com about four months ago. After chatting online, we spoke once via Skype. He lived a few hours away and was interested to go to dinner the next time he was in town. I agreed.

The date for dinner came and went. He never called. We never met. I wasn’t bothered or hurt. I barely knew him, so it was okay to me.

But here we are again – talking. He’s asking me basic questions that I know we discussed before. I know he’s a smart guy. He must remember. I wonder if he’s planning to keep this up all night. Finally, in a moment of quiet time, he says, “I met someone who looks like you recently. We spoke via Skype.” I replied, “that was me.”

He immediately turns to my friend and the couple and exclaims, “You guys! You will never believe this. I’ve met her before. We met on Match and spoke via Skype a few months ago. I was supposed to take her to dinner and I didn’t. I thought she was going to call me, but I guess she thought I was supposed to call her!”

Then, he turns to my friend and says, “You failed! I already know her. Just kidding…”

Wow. It has just been disclosed to everyone that I’m both using online dating, and that this person stood me up. Awesome. Even better, the entire group wanted to break apart the entire situation, and talk about my life as an online dater.

They also wanted to talk about how sometimes miscommunications can just happen and this is our second chance at love. Oh my.

Then, the doctor looks in his phone and can’t find my phone number. Ironically, his number is still in my phone. He says to me, “I can’t find your number in my phone. You must have given me a different name.” A different name? I mean, I have heard that some people do this, but I’m not one of those people. I give my own name. If it doesn’t work out, that’s fine, but at least I’m honest. So I said to him, “No. I gave my real name.” He insists that I must have given a fake name. Wow.

At some point, he goes to sleep (this party is taking place at a house). My friend takes the opportunity to try to convince me that I should give the guy a second chance. I’m sure my friend meant to best, but I wasn’t terribly disappointed the first time it didn’t work out. I’m not going to be terribly disappointed if it doesn’t this time either.

Anyway. Around the same time, the couple notices that the friend and I have a possible connection. The man leans in and whispers in my ear something like, “you’d rather date your friend, wouldn’t you?”

As if the night couldn’t get more awkward, it did.

Finally, I had the opportunity to go home. It was a nice attempt on everyone’s part to try to set me up. But, it was one of the strangest nights I’ve had in a long time. I look forward to these kinds of situations coming to an end.

It seems though that the only way for them to come to an end is to keep dating, and hope to eventually find someone you click with. Fingers crossed it happens sooner than later.