Carolyn Hax readers give advice to a 24-year-old starting to date

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We asked readers to channel their inner Carolyn Hax and answer this question. Some of the best responses are below.

Dear Carolyn: I’m 24 and had a really controlling upbringing. My rigid and overprotective parents effectively crushed any chance of me having a social life. Until recently, I worked at their business and they kept tabs on me all the time. Even in my 20s, they said I could only have a boyfriend if they picked him. Their choices were all awful: ugly, older men my parents said could provide for me.

They thought I’d never break away, but I found a website with help and advice for people like me. Now I have my own job and can provide for myself. I used all the money I secretly saved to move out and get my own place. I’m free! It’s blowing my mind that I can date anyone I want to and can eventually have sex for the first time.

However, my friends keep warning me that I’m really naive and guys are going to try to take advantage of me. Just this week, guys were flirting with me at work and the grocery store. How am I supposed to respond to that? How do I dive into the dating scene without getting taken advantage of?

New To This: How do you respond to that? However you want to! Your question hits home with me because I also didn’t really date until I was your age (my first kiss was at 23). My first relationship did take advantage of my good faith and resulted in heartbreak and cheating. However, I never considered that any of that was due to my “advanced age.” If anything, I felt empowered to end unpleasant relationships (something no one in my family had ever done) because I was older.

I was new to dating, but I knew myself and liked myself. I had developed many fulfilling nonromantic relationships. I felt I was uniquely qualified! Ultimately, I was able to be in a healthy, honest, easygoing relationship before many of my friends — not that it’s a contest — because I had no romantic patterns or “types” to fall back on. I definitely wouldn’t have chosen my husband when I was in high school. And that’s a good thing!

Your friends may have good intentions. It’s always good to keep one eye on your blind spots, especially when you have a history of controlling role models. Check your gut if anyone isn’t good with “no.” But I really believe you’ve got this! You’ve done so many harder things, and you should have faith in yourself.

New To This: I would start with double dates. Bring a trusted friend and their partner with you on a few dates. It will help ease you into the idea of dating without any pressure to do or say the “right” thing. If they aren’t into that for a first date, then they are probably not what you are looking for. When you meet someone nice and funny who is someone you connect with, then you try a solo daytime activity first. Like mini-golf or going to a museum midday. Go on a few dates like this before you think about an evening date where things might go a bit further. Hopefully, by then, you will feel more comfortable!

I also suggest you set up a sort-of “get out safe” system on your first date alone with someone. Have a friend call you 20-30 mins into the date. If the date isn’t going well, then you can say you have a family emergency you need to attend to; if it’s going great, you let your friend know and continue on the date. I hope you enjoy this exciting next chapter of your life.

New To This: Ask yourself this: How did you not get taken advantage of when you got a job or when you found an apartment? How did you know the job offer was fair, and the working conditions were suitable? How did you determine your living situation was safe and affordable? I assume you used the same self-analysis, critical thinking, and instincts you used when you decided independence was your key to living a full, happy life. So use that. Know yourself, and trust your instincts. Know what you’re okay with and not okay with, and set clear boundaries. Apply the same cautions as you would if you were starting any other relationship — even experienced people get taken advantage of if they’re throwing caution to the wind. Don’t be afraid to say “no” and keep looking. And don’t beat yourself up if you say “yes” and it turns out not to be the right person. Dating itself is a process of finding out about yourself and what you want as much as it is about learning about other people. Congratulations on your independence!

New To This: I found myself in a similar situation to you heading into college. As the daughter of two strongly Christian parents, there had been a lot of roadblocks for me to the kinds of fun that others my age were having, and suddenly all that fell away when I went to college. It’s not easy going from rigid structure to complete freedom!

I sought out advice from other women in my family on what to do regarding guys, and my aunt gave me the single piece of advice that kept me in a good frame of mind for that whole transition: Know what you want! If you know who you are and what you want, none of the other challenges can faze you, because you’ll have that foundation for making decisions. Do you want to meet lots of new guys in a freer atmosphere? Are you looking to jump straight into a more meaningful relationship? Your base judgment can help you decide which guys you like and which you don’t. Just remember what YOU want.

Every week, we ask readers to answer a question submitted to Carolyn Hax’s live chat or email. Read last week’s installment here. New questions are typically posted on Fridays, with a Monday deadline for submissions. Responses are anonymous, unless you choose to identify yourself, and are edited for length and clarity.

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