Don’t Make These Mistakes When Trying to Meet New Single People

Updated on May 29, 2023

Looking back on my dating life, there are some mistakes I made which prevented me from meeting more qualified people to date. This is a personal list, so these won’t apply to everyone, but I hope you’ll find something helpful here. If I could go back in time, I’d fix these top five dating mistakes of mine.

1. Not Having a Wingman or Wingwoman When Going Out to Meet New People

It was only later in life when I realized the importance of having a wingman (or wing-woman) when trying to meet new people. A wingman is so critical to provide motivation, keep you in a good mood, and keep the conversation going with new people that you’ve met (who usually are in groups). Plus, being with a friend makes you appear way less creepy when you’re approaching strangers. Make sure your wing-person understands why you’re out and how to help you meet people!

Women usually go out in groups so they don’t have this problem, however, they often end up being “closed off” in tight circles of conversation which are nearly impenetrable. That’s great f you don’t want anyone else to talk to you. But, if you want to meet new people, don’t be so focused on each other all night. Break up from time to time. Go to the restroom separately. This will make it much less intimidating for guys to meet you.

2. Not Cultivating Social Circles

What does this mean? My approach to dating was to be really “focused” on women that I was interested in. That’s totally wrong. It’s important to have a large network of friends of both genders and all ages. These friends can be wingmen/wingwomen, they can invite you to parties or other social events, or you may meet one of their friends who you want to date. Having a good network of friends is really important if you want to meet quality people, especially if you’re not into meeting people in clubs and bars all of the time.

3. Not Taking Enough Risks

I’m a pretty risk-averse person, not a thrill-seeker at all. But, dating is all about taking risks. A high-quality person won’t just land in your lap (the possible exception is Internet dating, but I never had much success with that).

Talking to a stranger that you’re interested in can be downright scary, but really, you have nothing to lose and everything to gain!

Just before I was moving out of town, I threw caution to the wind and started asking out all of the women I was interested in. The first one shot me down. But the second one didn’t, and we dated for a year (long-distance for most of the time). What if I had had this gung-ho attitude more often?

4. Not Getting Help with Clothes

This one is really embarrassing. I hate shopping for clothes. As a result, I did it as infrequently as possible, and as quickly as possible. I also hate asking for help, so I’d grab something off the rack and get out of the store as soon as I could. But later, a girlfriend of mine pointed out that a lot of my clothes were too big for me.

The moral of the story is to get help from salespeople when shopping for clothes. Or even better, bring a friend along. I wish I had brought one of my female friends to help me – that would have made all of the difference! Plus, maybe it could turn have turned into a date!

Check out these additional tips for people like me who hate shopping for clothes but want to look great on a date.

5. Fixating on One Person at a Time

Before I knew better, when I got a phone number, I’d stop trying to meet new people until I got to go on a date with that person. The result is, that date had everything riding on it; if I messed it up, I was back to square one.

Instead, even after you meet someone you like, keep trying to meet new people. Keep going out. The person you met might flake out or never get back to you. Don’t fixate on one person.

Having lots of options means you’ll always have a backup plan if someone does flake out.

Plus, you’ll be much more relaxed and not seem desperate when you do go on the date. If it works out, then great! If not, well, you’re going to go on a date with someone else in two days anyway.


I hope my mistakes will help you in your dating life to meet that special someone. What are some of your biggest dating mistakes? Please comment below! – Brian

Get the latest date ideas in L.A.

Subscribe to my posts. No ads or spam, Unsubscribe anytime.

Join 472 other subscribers

Or, join me on the LA Date Ideas Facebook Page or on Instagram!

Related Articles

Nine Things To Do If You’re Single in Los Angeles and Hating It

Nine Things To Do If You’re Single in Los Angeles and Hating It

Even though there are millions of single people in Los Angeles, it can be a tough and lonely place for a single person. Making new friends can be difficult, much less meeting quality people to date. Most people don't even know the names of their neighbors or fellow...

Ten Ways to Meet Single People During the COVID-19 Shutdown

Ten Ways to Meet Single People During the COVID-19 Shutdown

Dating doesn't have to stop during the quarantine I read an article about how a guy got to date a young woman that he saw from his window by sending his phone number using a drone! These are strange and grim times, with a terrible disease threatening us and many out...

6 Tips for Meeting People When You Go Out in LA

6 Tips for Meeting People When You Go Out in LA

After many years of dating in L.A., I feel like I've learned a thing or two about how to meet people. Recently, I thought, "what I would tell myself if I could go back in time and give my younger self advice on how to meet more people when I went out?" I came up with...

The Hottest Places to Meet Single People in Santa Monica and Venice

The Hottest Places to Meet Single People in Santa Monica and Venice

The Venice/Santa Monica area is one of the most popular parts of Los Angeles county to meet single people. You'll find lots of young, beautiful, successful men and women in their 20's and 30's here. So, check out my list of the top ten places to meet single...

How to Meet People at a Party Where You Hardly Know Anyone

How to Meet People at a Party Where You Hardly Know Anyone

It can be very intimidating to go to a party when you only know one or two people. You might feel awkward and tempted to leave early. I know I have. But if you bail, you'll miss the chance to meet new friends and have a good time. Here are some strategies to have a...

Ask Me a Question or Leave a Comment

Notify of

This site uses Akismet to reduce spam. Learn how your comment data is processed.

Inline Feedbacks
View all comments

Pin It on Pinterest