(Or, am I over thinking everything)

There is a girl (Jen) that I've been acquaintances with for about 3-4 years. I recently asked her if she would be okay with me getting to know her better. In my mind, this puts the scenario at me having an interest in her, but perhaps not the other way around (though she is willing to at least consider me).

This brings me to the crux of my issue, anything I can think of doing from here out seems very artificial. A casual lunch/dinner is an easy one, and so is a movie (though I'm told these are actually bad ideas). But after that, I just can't wrap my head around how I can make the random date ideas (that the internet seems to think are good) more natural. They make sense if there is a mutual interest, people are happy to do anything with the person they like, but without that interest "Hey, wanna go.... people watching/to a cooking class/do some other random activity that is completely out of left field with me?" seems like a very good way to bore Jen.

I figure that until Jen has an active interest in me (refer to bolded statement), the interactions should at least be non-awkward and be interesting enough to let her have an enjoyable time. So my question is, how can I make these intentional one-on-ones seems more natural?

(To be clear, I'm not asking "what should I do", but "how should I do it")

  • What do you mean by organic? What are the criteria that make something more or less organic?
    – sphennings
    Apr 19, 2018 at 20:09
  • As opposed to artificial. I should probably change the title
    – charlie44
    Apr 19, 2018 at 20:23
  • What do you mean by artificial? And don't say "not organic". :p
    – sphennings
    Apr 20, 2018 at 12:03

7 Answers 7


The easiest thing is: be genuinely interested in Jen, her personality, her ideas, life, etc.

Come up with something simple - like a night market. Go explore foods there, chat, listen and ask questions - enjoy the time yourself and give her space.

So many people try to learn how to be interesting to people, learn some communication tricks, gestures, techniques, yet most forget the basic rule - you really have to be interested in that person as a human being. Care about their emotions and followup on the topics they spoke about in the past.

Once you are genuinely yourself with real interest, Jen will feel it, and might become interested herself. Or she might not, but that's her right. If you try to over impress and show who you are but you are not( :) ), it most likely will be visible on subconscious level.


What does she like to do? What do you like to do? That's the first starting place I'd choose if I were in the dating pool again.

I think that people get weird ideas about dating. A date doesn't need to be some magical thing - it's really about the two of you spending time together where you get to know each other better. Seen that way, you can start inviting her to do things you might do anyway: "Hey, I'm going to the nature center for a little bit. Want to come with?" "The conservatory has a show of night-blooming avunculars. Feel up to it?" "There's a boat show in town. Feel like grabbing some cheap mini-donuts and looking at pontoons?" "I'm going to take a bread-making class next week. Would you like to join?" It's about an activity you both enjoy - focus on that FIRST, and then worry about whether she likes spending time with you.

If it's something you enjoy as well, then it's pretty much risk-free. So she decides midway through that she's bored and doesn't want to spend any more time with you. You still had a good time and got to do something you liked. What's the harm with that?

I'd also challenge your last sentence. Who cares whether it was accidental or on purpose? If some person who I knew as a friend wanted to spend more time with me, I'd take it as a compliment. "Sure, I'll go to the Stereo store with you. I'd like to spend some time with you."

Let Jen develop an active interest in doing things with you, and the active interest in you will develop. She'll see you as a person that she has a good time with, and the rest will flow from there.

  • Yeah. If you want to date someone, you have to let them know you're interested. Trying to be too subtle can easily backfire. Apr 20, 2018 at 7:03

Focus on yourself

A lot of these answers suggest various ways to find our more information from her, to try to guess what she will like and build a date around that. These aren't bad suggestions, but I don't feel they will get around your feeling of it being "artificial" - doing something you wouldn't normally do.

What I recommend you do

I recommend you pick something that you've always wanted to do, or have done in the past and found fun - regardless of whether she would like it, or whether she would even be the person you're taking.

That means if you enjoy museums, go to a museum you like. If you like coffee - go to your favourite coffee shop. Whatever interests you have, go with those - that is who you are, and you know you're going to have fun and be comfortable doing it.

Doing things you like, that show things about you, means there is no artificial element to it. You can truly be yourself, and if she likes that (and you like her) then that's great - if not, it would have been worse to delay that by pretending to be somebody different.

What is the IPS skill here?

The most important part of this is to accept that not everybody will like who you are, but trying to fit into their standards will not make you or them happy. This applies to any situation where you have values or interests, and want to see if somebody else has similar views - you should not change who you are to try and appease them.

In this specific situation, doing the above will help you achieve your underlying goal more easily as well though.

Since you want to get to know each other better, you should focus on showing her who you actually are. You will naturally find out who she is, and what her interests are while doing this, and if things are to work out - she will also want to take you places that interest her. Eventually you will find common ground that you both enjoy (and if you don't, you can just accept that she isn't as interesting as you thought).

Don't get into a "prove yourself" mentality. You are an individual, with interests and opinions, all of which are valid. You don't need to try to appease somebody else, or try to make them interested. Be yourself doing things you enjoy, and let things naturally progress from there.


You don't have enough information to be able to suggest something of mutual interest. So you have to ask.

Ask her if she would like to catch a bite after one of the meetings. Use the casual date to gain the info you need!

Then, ask her questions.

Things like what she does for fun, movies she has enjoyed, what her family and life growing up was like, and in between talk about things you like and want to do. In the conversation if you know there are events coming up, that you are interested in, ask if she would like to come with.

Because this isn't just about you getting to know her. It's also about her getting to know you. And if the things you are interested in don't interest her in the least, you should probably figure that out quickly.

One of the fun parts about dating someone is that your world is opened up to experiences you might not normally have. Some people are down with that. Some people only want to do stuff they already know that they like. A mix of both is best for all involved.

If you go alone with her to an event there is a certain amount of social pressure surrounding something like this, so if you have a group activity or party or whatever to sprinkle in amongst the specific "date" scenarios, she will be more comfortable.


There is a girl (Jen) that I've been acquaintances with for about 3-4 years. I recently asked her if she would be okay with me getting to know her better.

As you have been an acquaintance with this girl, your friendship groups etc. should tell you what areas you have in common and whether you really get on or click.

It sounds like you have a confidence problem and are not sure what you are looking for in someone else. I would suggest you start developing friendships with people and discover what you like and enjoy in others. Going to groups where there are common goals helps and learning to develop situations which are encouraging and enjoyable. Once you have these skills, developing more intimate relationships with people will become much easier.


I have found that if a girl is interested in a guy, any activity is acceptable for a date. The girl is interested in the guy, not the date, unless it's something spectacular, like a trip or a concert. Then she might agree even if she doesn't like the guy.

Most girls like a take charge kind of guy; a guy who just knows the right thing to do; a decisive, confident male who knows what he wants and how to get it. If she says, "No, I don't want to do that", that means she's not interested in pursuing things.

When a girl wants to be just friends with a guy, it means she likes him, but she wouldn't mate with him. If she was willing to mate with him, she'd want to be more than just friends.

So, I think you should invite her somewhere where you can build her a fire (the beach is always good), and share a bottle of wine together. What could be more natural. Just take it one step at a time, and enjoy yourself with her.


I don't want to read too much into what you already said to her, namely...

would [you] be okay with me getting to know [you] better?

... but that does kind of imply that you don't know her particularly well right now. Even after 3-4 years of being "acquainted" you don't know what sort of things she is interested in or what sort of dates she might like.

I don't know who told you that dinner dates or the like are a "bad idea". Perhaps overly formal dinners, yes. If she isn't quite in the place that you are yet then she might find the idea of dressing up or spending a lot of money on food a bit intimidating. But what you need in order to "get to know each other better" is time to talk, and a casual dinner date or similar might be just that. You can't talk during a movie, and until you do get to know her then you don't really know what sort of movies she likes.

So don't over-think the setting, just anything casual where you can talk.

Things you could talk about on the date:

  • Your backgrounds
  • Interests
  • Future goals

There is no exhaustive list but where you came from, where you are now, and where you are going are pretty much what we need to know about people we might want a relationship with.

Some "don'ts":

  • Don't just methodically work through that list of topics above. Natural conversations go off at tangents that they may never return from. Let her talk about whatever she wants to talk about, just use questions as a starting point. If things go well there will be another date, and another time to learn more about each other.
  • Don't try to force the idea of you being in a relationship into the conversation. For example if you talk about future goals, don't start asking about marriage, kids, or if she can see a future with you.
  • If talking about the past, don't get into talking about previous relationships if possible. This isn't good first-date material. There will be a time for this.

Lastly, don't overthink it. "Getting to know" one another may lead anywhere. It may not lead to a romantic relationship. So just let conversation flow and don't try to steer it in any particular direction.

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