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Ask HN: How to have a meaningful conversation with a date?
17 points by rex_lupi 56 days ago | hide | past | favorite | 11 comments
This might seem like an out of place question to ask here, but I'm sure there are folks here on HN who have experienced something like this at some point, and I believe the people who would understand my issues best and would be able to provide actually useful tips can be found here.

I possess the typical hacker mindset with interests and passions that are not so "popular". I'm socially awkward and bad at talking, especially so when I don't have much in common with the other person. I don't think I have a good sense of humor and I tend to have a cynical and pessimistic outlook on things, i.e I'm not what one would call a "fun guy". So I run out of topics to talk about and the conversation quickly becomes boring for both of us, even though we're genuinely interested in each other.

Please note: I won't be taking "Find someone else" as an answer.




Take care about your grooming, clean nails, trimmed eyebrows, clean and fresh clothes.

Most people can talk easily about themselves, so if she doesn't have anything to fill a silence, general, open questions like, 'so, where did you grow up?' will get you over it and produce new content, as it were, that can lead forward. You can contrast or note similarities, but don't take over the flow unless asked about something or it's silent for a while.

Things in common are good but you don't need a carbon copy of yourself, you need someone compatible enough to get along with each other, and the hardest thing, both need a partner they can respect and trust.

If both sides feel further research needed, meaningful conversations will present themselves as it goes on. If either side don't feel it's good, be kind and accepting, she's putting herself out there same as you; if you learned a deal-killer, you'd be in the same situation having to gently detach. At the same time, if it's your feeling, you need to indicate that you would like to go on, so people typically propose doing 'it' (the date) again, or suggest going somewhere specific together at the weekend, so it can be turned down cleanly but also to show clearly where you are at.

Good luck.


Any "advanced version" of this question? I see pretty good beginner answers, but what if I have no problem holding a conversation and I just want to go deeper?

And my contribution: approach the date with curiosity. Try to find out what their story is. Other than that, make a reflex to avoid questions that can be answered by yes/no. They will turn the conversation into an interrogation.

Also, don't be afraid of pauses. In a date, conversation is actually the filler - attraction is created by the tension in the silences.


You don't need to talk, what women (and men, and people etc) in general really want is someone to listen. And actually actively listen. Show interest in them.

There might be more but off the top of my head there's some books may help

Attraction Isn't a Choice ( https://book4you.org/book/3630830/fb2ebd )

Double Your Dating: What Every Man Should Know About How To Be Successful With Women ( https://book4you.org/book/1074199/4cfbfd )

Talking from 9 to 5: Women and Men at Work ( https://b-ok.cc/book/2860541/513708 )

You Just Don't Understand: Women and Men in Conversation ( https://b-ok.cc/book/1264063/e970e0 )

Obviously buy them if you can and think they're worth it. Don't be put off by the titles, they are actually insanely good. Good luck!


Celeste Headlee's "How to be a good conversationalist" is a good start:

https://youtube.com/watch?v=R1vskiVDwl4

https://www.npr.org/2020/10/15/923962314/good-conversations-...

Summarized:

1. Don't multitask. (4:27)

2. Don't pontificate. (4:50)

3. Use open ended questions. (6:02)

4. Go with the flow. (6:39)

5. If you don't know, say that you don't know. (7:26)

6. Don't equate your experience with theirs. (7:46)

7. Try not to repeat yourself. (8:26)

8. Stay out of the weeds. (8:46)

9. Listen. (9:08)

10. Be brief. (10:29)

I'd strongly emphasize the listen part. It's not your sole responsibility to direct the conversation (and that ... gets old). The art lies in discovering the topic together. Prompting your companion often leads to the most interesting discussions.

And yes, often, what you'll find is that compatibility is limited.


If you think about yourself as the cynical, pessimistic, humorless guy, then that is what you will project. Many people find passions fascinating, even if it's something they themselves are not directly interested in. But if it surrounded by a dark cloud, even the most relatable conversation topics will be draining. Misery loves company, and if you are a negative person you will only find other negative people in the long run.

Humor is a learnable skill, but it needs to be practiced with people. My number one tip in this area is that if a group doesn't laugh at a joke the first time, they will not laugh the second time. My observation of many awkward people is they over emphasize delivery in humor, and think that if they say the joke the louder the second time, then people will laugh. That is usually false. They heard the first time, and were polite enough to move the conversation forward while overlooking your faux pas. Don't expect that kindness a second time.

Social personality is just as hackable as any other part of your life, but people are afraid to do it because they feel like they will lose themselves. You might lose yourself, but you may just as easily discover a new self that you like much more. At that same time, those traits that you use to describe yourself may actually be symptoms of depression or other unresolved issues. Talk to a therapist either way, they can help with developing skills, and may help you resolve those things that force your thoughts to darker places. Changing takes a large amount of self-reflection that is next to impossible to do alone. Therapists are going to be a better resource than any quack youtube channel or self help guru peddling Sigma mindset or confidence building bullshit.

Finally, look to better yourself in all social context, not just romantic scenarios. People can tell you are being performative, and will notice that you act one way towards them and another towards others, and may see this as a red flag.


If you're serious about learning and looking for people who have gone on the same journey, dive into https://www.sosuave.com

Please note: Having social success with "someone else" (doesn't have to be sexual, although that helps) will often make the person you're interested in _more interested in you_. This is known as "social proof". Also, beware of oneitis, the literal disease of getting obsessed with "the one". There is no such thing as "the one". That's a Disney/cultural fairy tale and it can/will eat you alive if you let it (which is precisely what happens when you don't/won't take "find someone else" as an answer).


I find the "date setting" quite difficult at times. To improve I signed up for various meetups, like hiking groups and such, so I could meet lots of people and talk without the pressure of being on a date.

I often ask about what they've studied or what they work with, trying to find their interests and passions. I'll use that to probe further, maybe asking them to explain something or give their opinion on something I've picked up elsewhere.

I'll ask about hobbies and what kind of movies they like, fertile grounds for finding something in common.

To give them a chance to initiate something, I'll also let the conversation hang a bit every now and then.

Still don't feel comfortable at the date thing, but at least it's easier to talk to people.


Maybe try and organise a date where the event generates conversation. Like bowling. Or go see a movie before going for a meal.

Ultimately though, if you’re bored of each other’s company then you’re not suitable for each other. So the “find someone else” answer, while not what you’re after, is perfectly apt. Just remember that while some people find it easier to form connections, it doesn’t mean they find it any easier to find love.


I think the right girl will appreciate your ecentric nature. In fact girls want someone unique and esoteric that they have to unlock.

So just be yourself, keep the conversation light and more about her interests and you’ll gradually find that you’ll reach a flow state.

Pro tip- always helps to have some funny Tik Toks in your back pocket to lighten the mood.


> In fact girls want someone unique and esoteric that they have to unlock.

It’s best not to generalise ~50% of Earths population ;)


If the conversation is not working by itself, you are with the wrong person. Period.




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