Relationships

What I Wish I Knew About Dating in My 20s

Dating in a time when choosing the right person involves swiping through images of potential dates and communicating via text (what does the message “hey” really mean after not hearing anything for 3 days?) can be brutal. I may be a married 30-something, but I spent the ages of 28-32 dating (mostly online) and met my husband on Tinder, so I know a thing or two about how it all works. Here’s what I learned dating in my 20s and 30s that I really wish I had applied to my 20s (and early 30s, too).

He’s probably not that great

That sound so negative, but it’ll all make sense in a minute because I was the queen of going on what I thought was a great first date and then building a guy up to be so wonderful and amazing before really getting to know him. I’d give him so much power over the situation by doing that, just sitting back waiting to hear from him. Maybe he wasn’t that great (he usually wasn’t) and wasn’t worth dating. There were obviously way more dates that ended with me wishing I hadn’t put pants on and left the house, but there were definitely a handful of idiots that I gave way too much credit to far too quickly.

The lesson? Get to really know someone before deciding he’s worth dating. Guys love going dark for a few days or better – saying they had a great time and never reaching out again. Why do we do this? Or maybe “we” don’t and it was just me. Hopefully you know better.

Even if he’s nice, handsome, and seems wonderful, it’s unreasonable to decide he’s relationship material after just one date. Learn more about the guy. Who he is, what he’s about, how he treats people, and what he’s looking for. Give yourself time to actually get to know him before deciding how great he is.

He’s not that busy

I’ve seen friends go through this one so I can tell you I know it’s not just me. One friend made up every excuse under the sun for a guy who was clearly not that into her, and she was basically the only one to reach out and carried that “relationship” for months.

The classic not hearing from a guy for a week and either believing his excuses or making excuses for him. We’ve all been there, right?. If a guy likes you, he’s going to reach out and is going to want to see you. If he’s too busy, he’s either not interested or has a secret wife, baby, or girlfriend he isn’t telling you about (because that actually happened). I’d usually let the guy reach out first and then feel like it was ok to start another conversation after that if things were going well. I hate hate hate games but didn’t see that as a game. It was me giving a guy a chance to reach out, and if he didn’t, it was a sign that he wasn’t right for me.

Games are the worst

If you want to text someone, text them. Not again and again, and don’t be the only one to start a conversation, but if texting a guy is reason for him to end things, he’s not looking for a relationship. One of my guy friends told me he’d be happy to hear from a girl he liked, and that if the guy isn’t replying, he’s just not that into you.

Slow down

I’m over here writing this post realizing how terrible I was at dating. There were 3 guys (Conor was one of them) that I dated and dove into relationships with pretty quickly. The two that weren’t Conor ended up being socially awkward, which I knew but they were both great guys so I kept dating them. Then both relationships became too much and I ended them. Had I paced myself and been a bit more of a realist (no one wants to date the guy who drinks half a bottle of tequila and speaks to no one at a party) I could have avoided ending those short relationships, which is just never fun.

I obviously don’t regret diving in with Conor, but I probably could have paced myself a little bit. For reference, we had our first date on a Tuesday and I met his mom that weekend. In his defense, he wasn’t like “ok it’s been a great few days so do you want to meet my mom?” We met for brunch and he asked what my plans were for the day. I didn’t have any and he said he knew it was really early, but he was going to meet his mom and stepdad on a boat, and invited me to join. We had just met so there wasn’t any pressure (also boats are fun) so I joined him.

Back to my point. When it’s right it’s right, but if it is the relationship you’re going to be in for the rest of your life, why not pace yourself a bit? Spend time with your friends, spend time with yourself, and enjoy those days when everything’s exciting and new.

No one is too busy to say hi for 3-5 days

I touched on this but it’s a big one so let’s talk about it again. Unless he’s a heart surgeon and in surgery for days or building houses in a remote village across the world and has absolutely no phone access, there’s really nothing that will leave someone so busy they can’t reach out and say hi.

Early on in our relationship, I traveled to LA to speak at a workshop and while I was there, Conor had to fly to Atlanta to see his dad. I had just stopped seeing the guy with a wife, baby, and girlfriend so naturally I went to a dark place and Conor was beginning the phase-out. I told you I was bad at this dating thing.

It’s ok to be upfront

No, you should not go on a first date and say how badly you want a relationship and you should not try to figure out your relationship status on or directly after a first date, but I think it’s ok to make it clear that you’re looking for a relationship (with the right person). These days, people are often looking for something “fun” or short-term, and it’s best to find out if you’re on the same page sooner than later.

Stop settling

When I dated that guy with the secret life, we were driving to dinner one night and he told me he felt like he couldn’t give me what I wanted (a relationship). My 20-something self would have said how I wanted to make that work with him but my early 30-something self just said something along the lines of “ok, well I want a relationship and if you don’t that’s fine, but we shouldn’t keep dating.” I gave the idiot such an easy out but he said he wanted to take things slowly. You know, because his life was one big lie.

If someone shows you who they really are or tells you what they want, save yourself the trouble and walk away.

I know dating isn’t easy and sometimes not dating someone can feel really lonely. Sometimes I’d be really into being on my own and not wanting to deal with the potential misery that comes with dating and others, I wanted to be in a relationship so badly. It’s really hard. It”s really important to remember 2 things.

1. You’re never actually alone, even if you’re not in a relationship. Focus on your friends and yourself.

2. It’s better to be on your own than to spend time with someone who doesn’t appreciate you and want to be with you.

Are you in a relationship? Have you tried online dating? Tell me more in the comments below!