No Stupid Questions

I met my wife dating online. Before that it was brutal. Lots of ignored messages. Lots of messaging that just ended (often on the woman's end, but sometimes on my end). And plenty of first dates.

When I first started dating I wasn't picky. Basically any girl interested in me, I'd show interest. Eventually I actually applied myself to dating with purpose. This helped a bit as I was often times being the one to make the decision whether or not to even meet up with a woman. I made sure they met my criteria and wanted the same things as I did. And doing this required that I was honest with myself. I didn't want to party, I wanted children, I wanted someone who would challenge me and call me out on my bullshit, but I also needed someone who wasn't overly sensitive as I am often quite blunt and speak without thinking.

Basically I had to shift from wasting my time with anyone to getting right to the point and making sure our values and trajectories in life aligned. This filtered out a lot of women. Either immediately because we didn't want the same things or because they were put off by my directness.

Dating sucks. For every nice person you meet and make a connection of some sort with there’s three or four who drop off the face of the planet. I get it’s easier to just ghost but it’s pretty shitty. (And this is speaking as someone with social anxiety who has definitely ghosted before lol oops)

Hey OP, I hear your frustration. Sometimes, she will simply not be into you like that, and that’s okay. But there are concepts that can significantly improve your dating life if you learn them.

The most important thing is to intentionally be romantic. You have to flirt. The way you describe this interaction doesn’t sound very flirty. She was nice and you had a good conversation? That’s great, but she could probably get a similar experience from a friend.

Flirting is about making things exciting. Taking a risk and making your intentions known is often attractive. Think playful banter. Having a low stakes, interview-style conversation is just boring for most women.

Practical ways to be more flirty:

• choose a venue where you can sit side by side
• maintain great eye contact when she’s talking
• don’t rush to fill every silence, let it breathe
• use statements more, rather than just questions
• respectful and appropriate use of touch
• playfully challenge or disagree with her at times
• humor is great, but don’t constantly joke around

Basically, being a nice guy with a good job is great, and actually a prerequisite for many women to date you. But it’s not inherently sexy. You gotta learn how to embrace your romantic side to show them you’re capable of that, too.

Dating through an app is hard. I can't hack it at all. Dating through mutual friends will limit your options, but genuine connections happen much more readily. I've found (what felt like) true love a few times, all from mutual acquaintances. I didn't have a good job, and I'm not even that nice (or "nice") of a guy IMO. I just made normal friends, and dated the people they knew.

You don't need to compete with the whole world of sexy, highly eligible, rich people. You need to be a person with friends, not habitually smell bad, and be capable of genuine human vulnerability. That's literally it.

I had a friend who was having problems with dating. Specifically his online dating wasn’t going well, and while he was a super outgoing person, he wasn’t the kind of guy to pickup a woman at a bar. Anyways, I told him to first think of his target demographic. What do they look like? What are their hobbies? What’s traits, characteristics, and thoughts do they have that you look for?

Once you know who you’re after, then write for them. Treat the space on your profile as a sort of open-ended love letter for a fill-in-the-blank style adventure. Maybe even make it an actual fill-in-the-blank as a sort of cool way for them to have interaction with the profile.

Another point is Algorithms, algorithms, algorithms! People forget that algorithms run our lives from HR filtering applications, to online dating. Have engagement on the site. Specifically by updating your profile regularly. That keeps the pictures fresh, the content current, and feeds the algorithm to boost you to the top.

Maintaining a relationship is always the fun and easier part, IMO. I’ve always told friends and family that relationships aren’t hard work with the correct partner. If someone ghosts you, it means they aren’t right for you, or it isn’t the time for them. As well, focus on keeping engagement with that person active. Just like algorithms on websites people love someone who is constantly updating, and staying current. It doesn’t have to be exhausting, but it does require some effort on your part.

Lastly what helped my friend the most was when I told him to scale back the nerd. To include it as part of your hobbies and a single picture, but having multiple pictures of you doing the same thing is repetitive, unhelpful, and only tells me one thing about you. Variety is the name of the game.

I wouldn't call it hard per se. I would call most current dating practices a waste of time. It's a lot like playing the lottery, but instead of money, I pay with my time. And even statistically speaking, the odds are quite bad, for both sides. When you have so many choices every choice seems less worth it. When you have too few choices, competition is fierce. I envy neither men nor women in today's scene, and I'd expect it to be much more difficult for the LGBT+ community.

I would say two things to you, not necessarily connected.

One, we think the grass is always greener on the other side. When I look back at my partnered life compared to my single life now, I would say my life now is better. After spending time with myself I was finally able to solve loads of internal issues. Relationships can become a very comfortable state and I definitely let myself go too often. I haven't forgotten that loneliness also occurred while I wasn't single.

Two, you can make no mistakes and still lose. As Picard said it best, that's just life. If life isn't working now, I wouldn't expect a partner to fix it. After the honeymoon phase, we tend to fall back to our old selves. Use this time to get that self in order and perhaps while you do it you find yourself happier regardless of the outcome of life.