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I’m 30 and I’ve never been on a date. Where do I start? Carolyn Hax readers give advice.

(Nick Galifianakis for The Washington Post)
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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 am a 30-year-old male. I have never been in a relationship or even on a date and have never had sex. I’m not even 100 percent sure whether I am attracted to women or men (or maybe both?) since I have never had a romantic experience with anyone of any gender.

I would like to try and experience some of these things, but at this point I am trapped in a vicious cycle of my own making. The longer I wait to put myself out there due to fear/embarrassment, the more awkward it becomes. Yet, the more awkward it becomes, the less willing I am to try.

I did attend a few therapy sessions to talk about these issues, but I stopped going due to the pandemic. The therapy was helpful, but the onus is still on me to take the initiative if I really want to experience these things, and I feel time slipping away. What can I do?

— Lost About Love

Lost About Love: I hear you! I’m a woman in my 30s and didn’t date or have sex with anyone until I was almost your age. I’ve since been in exactly one serious relationship and am currently single. Here are a few thoughts from this side of things:

1. You’re totally wonderful and dateable exactly as you are. I think we spend a lot of time in dating rewriting our insecurities as insurmountable flaws. “I feel insecure that I haven’t slept with anyone” can so quickly become “Nobody will ever want to date me because I haven’t been in a relationship, had sex, etc.” Dating involves facing possible rejection from people we’re into, and it can feel easier to reject ourselves than open ourselves up enough to experience that possible sting (and, on the flip side, some excellent dates). It helps me to remind myself that these “flaws” are just what they are, my insecurities. The people you want to date will be happy to date you as you are, whether your relationship history is a single blank line or hundreds of pages long.

2. Figuring out who we’re attracted to is hard! It can be especially difficult when that attraction sometimes only comes once we’ve built an emotional connection with someone. For me, figuring out my sexuality was a bit of trial and error, including dating an amazing person and realizing, “Oh, you’re awesome! And I just don’t want to go very far physically with you because my body parts aren’t into your body parts.” As you date, you’ll gain lots of information about things you do and don’t like in a partner, including more clarity on who you’re attracted to on all sorts of fronts. It’s 100 percent okay not to know that yet.

3. Recognize that dating during a pandemic is weird for all of us! Some people will be less interested in meeting up in person, and others might just be too tired to connect because of other things they have going on in their lives right now. If you don’t hear from someone, it really probably is about them, not you. In good news, the barrier to dating is pretty low right now as you can set up an online dating profile for free in a few minutes if you haven’t yet or ask a trusted friend if they could set you up on a “practice date” with a single friend of theirs. Keep it casual (coffee or Zoom, not a full meal) in case conversation lags and recognize that dating, just like making new friends, takes time and energy and can also lead to some fun connections and great stories.

It’s a big world, and there are some amazing new people who’d love to meet you. Good luck out there!

— Been There

Lost About Love: I am a woman, and I didn’t start dating, have my first kiss, or have sex for the first time until I was in my 30s. I can’t tell you exactly why. I have always had a pretty normal social life — friends, activities — and while I’m not a beauty queen, I think I can say I am at least average looking. But it just didn’t happen for a long time, and it made me deeply unhappy. (There are more of us out there than you might realize!)

I didn’t understand why this experience that seemed so important and universal wasn’t happening for me. I did speak to a therapist, who helped me to process that, and I realized I needed to put myself out there more. I was complaining about something that I never actively pursued. (I think I felt like, “If other people can just meet someone without trying and get asked out, why can’t that happen to me?”)

Honestly, a lot of people may bemoan many aspects of online dating, and admittedly it has its flaws and it’s not for everyone, but it was GREAT for me. I just needed to get my feet wet. I knew if I connected with someone on the app, that we were there for the same reason. Because of my inexperience, I had become insecure in in-person interactions, always questioning myself or the guy. Was he flirting with me? Was this just friendly small talk? With online dating, you know what the other person’s intentions are — dating or sex. (Often both!) And with online dating, I just started going out on a bunch of first dates. This helped me to both get more comfortable dating overall, and learn what it was like, in a low-stakes way, to both get rejected and reject someone else. Learning to say no to someone in a polite way is a great dating skill.

I made some friends, had some good, bad, boring, and romantic experiences (first kiss on a train platform before he ran off to catch his train), and learned that there were people in the world who found me desirable, which gave me confidence. And no joke, though this is a maybe slightly unusual outcome, I started online dating in earnest in the spring of one year, and by the fall of that year, I met my fiance. I can’t promise online dating will bring you the love of your life, but what it could do is help you meet people, get more comfortable with the social dynamics of dating, and learn what you’re really drawn to in a potential partner. And it might even be fun! (At the very least, you will probably get some excellent stories out of it.)

— Late Bloomer

Lost About Love: It seems like you’re putting a lot of pressure on yourself because you think you “should” have experienced dating and sex when you were younger, so you feel fear and embarrassment because you haven’t. There are probably lots of things you haven’t done by 30, like hang gliding or water skiing or salsa dancing or whatever, and you might feel a little anxiety about trying one of those, but you wouldn’t feel embarrassed about not having done those things before. So why put unnecessary pressure on yourself over dating or sex? Try to see them as activities that you haven’t tried yet but you intend to cross off your list one day. When you’re ready, start mingling and make yourself available.

I think it might help to stop looking at it as looking for a romantic partner and just try to get out more and meet people. Take some classes or join some clubs that interest you and invite a few people at a time for coffee or drinks. Talk to people and listen to them, let people get to know you, find common interests and build friendships. If you share an interest with someone in the group, suggest getting together to do it, and that will be your first date. Dating is like auditioning people to see if you are attracted to them and whether they bring out the best in you. There’s no obligation to kiss or have sex just because you asked somebody out on a date. If you have a good time, suggest another date; if you don’t have a good time, ask somebody else next time. Maybe somebody in the group will ask you out. Some of the best romantic relationships grow organically from strong friendships. As you mingle more, you’ll learn what attracts you, and you can look for ways to meet people with those qualities or interests.

I know it can be difficult to find a therapist for in-person visits right now, but most of them are offering therapy by video calls. I hope you will look into that because it can really help you to get all your anxieties off your chest so you can just have fun with your new friends and potential partners.

— DaffySez

Lost About Love: I can’t tell from your question if you are saying that you have never felt romantic feelings toward someone at all, OR, if you are saying that you do experience romantic attractions but haven’t had the courage to “go for it.” In my mind, this is what makes all the difference.

If it’s the first one, that you genuinely don’t experience romantic/sexual attraction toward people, you might find real comfort in the “ace” and “aro” communities (asexual and aromantic). There are lots of cool people there you could connect with about what you do want your life to look like — including things like intimacy, companionship, etc. — if the traditional notion of “getting swept off your feet, falling in love” just isn’t how you’re wired to relate.

On the other hand, if the issue is that you feel romantic or sexual attraction but don’t have the confidence to put yourself out there, perhaps a trusted friend could help you put together some dating profiles and give it a whirl. I don’t think you have anything to be ashamed of, having not been in a relationship yet at age 30. I think when you are in “first date” mode, you could have something nonchalant to say when relationship history comes up — like, “To be honest, as a teen and young adult, dating held no interest for me. It’s only recently that that’s started to change. I’m really glad to be on this date with you!” (Changing the subject back to the other person and complimenting them is almost never the wrong way to go.) If something deeper starts to develop with a specific person, as you get to know each other and build trust, you can consider revealing more about yourself, how you’ve felt about romance in the past, your worries/fears about seeming to have a different path than others, etc.

— Dated/Overrated

Lost About Love: I was 29 when I went on my first date. I had a full social calendar of people I loved, I’d never really been romantically interested in anyone, and wasn’t sure how to initiate into that world since it wasn’t happening organically in my own social circles. I chose two online dating websites that I was most comfortable with, one related to my faith and one that wasn’t quite the open forum that others are and focused on matching interests and put myself out there.

I had a lot of first dates and then eventually second and third dates, began to see what I liked and valued in someone as more than a friend, and then I met the man I married. That lack of experience didn’t seem to matter to the men I met. And getting to know someone is getting to know someone, you have those skills already.

You got this. It’s scary putting yourself out there. And you’ll meet some people who aren’t a match, but you’ll meet a lot of great people who you like and like you as well.

— Jenny C.

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

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