Dating Tips for Inexperienced People in Their 20s

Dating Tips for Inexperienced People in Their 20s

This is for those who have never been in a relationship before, or don’t have much dating experience. You meet someone with good potential (maybe through online dating or from real life), and you’re nervous and want things to go well on the first date. Here are some tips.

Basic dating etiquette:

  • Be punctual (give yourself enough time to get ready, ladies!)
  • Don’t text
  • Try to have a positive attitude and be friendly. No one wants to be around a Debbie Downer, especially on a first date.
  • Be prepared to pay for yourself

Be a thoughtful conversationalist

Think of questions, as well as answers to possible questions, before you go on a date with someone. This is to avoid those awkward, on the spot responses that often happen when you are new at dating or maybe just awkward in general. Avoid giving one-word responses because those are boring. Really focus on the conversation and try to add to it.

For example, when your date asks, “How are you?” in the beginning, try to expand on “Good.” Say what you were up to that day.

When your date asks “What do you like to do for fun / in your free time?” give a list of things and hopefully he or she will be able to relate with at least one of them, giving you a common interest and thing to talk about.

When your date asks about past relationships (“So when was your last relationship?”), don’t mentally freak out because you’re embarrassed about never having been in a relationship before. Again, give a thoughtful answer. You could say something like, “Well, I’ve actually never been in a serious relationship – I've only casually dated," and mention how you’ve been focusing on other things or just haven’t found someone you were mutually interested in yet. Keep in mind that your inexperience is not a big deal if you don’t make it one, so just own it and own who you are. Have confidence.

Additional questions:

  • What do you do? / Where do you go to school? / What are you studying?
  • What are you looking for?
  • Did you grow up around here?
  • Do you have any summer trips planned?
  • What music do you listen to?
  • What are your favorite shows or movies?
  • Do you have pets?

For the guys:

If the date went well and you want to see her again, offer to pay. She will feel special and appreciate your chivalry.

An hour or two after the date, text her and let her know you had a great time. You could say something like, "Thanks for coming out with me tonight. I had a great time getting to know you :)" and if she's mutually interested, you guys can set up another date.


Most Helpful Guy

  • Good take. I can totally relate to this. I used to be worried that the fact I've never had a relationship would be a dealbreaker to women at my age even though I have dated but never had anything serious. It's all about how you say if. It's better to say I've dated but nothing serious as opposed to saying I've never had a girlfriend.

    The thing is I've had dates with so many women but usually the ones I liked didn't like me back and vice versa and my closest to a relationship was being rebounded which hurt like hell.

    One of the things I'm trying to find out is when do I reveal that I want a relationship without coming off as clingy or rushing? 3rd date? 4th date?

    • Thanks, I'm glad this helps. Hmm, it's hard to give a fixed date... I think the 3rd - 6th date is a good general range (anything sooner seems rushed, imo).

      Honestly though, whenever feels right. Whenever you get to the point where you get along really well, have fun together, and feel comfortable with each other. Don't over analyze too much -- things will fall into place if they're meant to.

    • Show All
    • Pls say you just have been looking but no one but that girl has caught your eye.

    • What? Yeah I've been looking and there's this girl from tinder I've had 3 dates with. I was just stating my experience prior to it.

Most Helpful Girl

  • Thanks for the tip on how to answer the "when was your last relationship" question. Much better sounding than "Well, no one else has found me appealing enough" :P

    • Bahaha, exactly! No problem. ^.^

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What Guys Said 8

  • I'm so nervous when it comes to this because I'm not much of a dater & I don't know what really makes women happy. But it's great that the others guys are doing everything they can to make their women happy everyday. Hopefully, I would be brave enough for me to fall in love & date someone without screwing things up.

  • No texting? How do you mean? If I were to be a few minutes later, should I call her up and tell her or is a quick text better? Or do you mean texting pre-date?

    • I meant don't text or play around on your phone during the actual date. It seems obvious, but I thought I'd mention it anyway!

      If you're running just a few minutes late, then calling or texting isn't necessary. If you're running 10+ minutes late, then I'd call or text -- it doesn't matter which.

  • Not bad, short and sweet, to the point.

    It's a shame that the "one word answer" thing as necessary to add, but unfortunately a lot of people do tend to do that, so it can be a frustrating situation.

  • What if the guy is shy?

    • I have been there myself but the girls that I have connected with I have usually felt comfortable around

    • @badger25 how do you find that connection, it always feels difficult to be what girls want.

    • trial and error man. I have always been especially nervous when it comes to asking girls out but I have made some connections through Tinder, Plenty of fish, coffee meets bagel, and other online dating sites.

      Its a good way to start a conversation with someone, then when you meet in person you already know you have some stuff in common

  • And then what do you do if you can't GET a date?

    • if this is directed to after you've already had the first date... then I say move on... I mean it sucks but hey, you got to know someone new.

  • @doctorwhofan forever alone... .

  • Yep I knew the sexist little jab about men paying first would be thrown in there at some point. It's almost a cliche' at this point just knowing it's going to find it's way in to "etiquette"

    • Like I said, basic dating etiquette is preparing to pay for yourself, meaning girls shouldn't just assume the guy will pay.

      But if offering to pay for a girl who you invited out and are really into on the first date (I'm not saying all subsequent dates -- just the first date) will make her experience better, then why not just do it? A first date can even be something cheap like coffee. It's just a tip; you don't have to follow it if it goes against your views or something.

    • Lol there's nothing sexist about saying its a good idea. It's never stated as a hard unbrekable rule.

    • Hahahaha all those fucking downvotes.

  • Times like this I hate being born male

    • I love being born female. But you know you can initiate, while I can only wait for the one to approach me.

    • That's something I resent, and unfortunately being bitter, resentful is a thousand times worse if you are a guy

What Girls Said 2

  • I went on my very first date a couple months ago.

    We talked about many of the topics and he seemed like a nice guy. Only he looked at his phone a little to much for my liking, & kept glancing at the TV betweem topics. I don't if it was because he was nervous or awkward. But that gave me the feeling he just wasn't interested and I havmt contacted him since.

    • In this age of tech, multitasking and short attention spans you'd think people would become more forgiving of such behavior.

    • Sure I wouldn't mind a glance or two, but when you actually pick up your phone and mess with it for like a mintue or two I find it a little rude. Call me old fashion but when I sit down to eat with someone I actually like to talk to them without the distraction of technology. I dont like it even when my family does it.

  • Gonna text anyways


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