I'm in my 30s and I've never been on a date before. What should I expect?

Question

What should I do? What should I say to him? Should I offer to pay my portion of the bill?

Just a little backstory. I've never been on a date before because I was raised in a very strict household and then once I went off to college, I became very studious and that continued on into graduate school.

Once I graduated, I went straight into the workforce and it became very hard to find time to go out and find someone to date. So I recently decided to go on a dating app and I matched with someone. We've barely chatted about anything significant. I don't know much about him other than the basics. He's an enigma to me which scares me. I don't know how to go into this date. I don't know if he is the funny type that likes to crack jokes or the serious type.

I'm leaning more towards the serious type as he hasn't really cracked any jokes in our convos so far. It's very bland.

I want to impress him, but I feel my lack of dating skills is going to deter me from being good at this. Help please!

SteveSmith1985 · Accepted Answer

Be careful. There are probably (almost for sure) very basic very common safety measures most women take. You need to familiarize yourself with these by asking other women, or even a google search I imagine.

For example, not letting a guy bring you on a date in his car (pick you up in his car), because then you can't decide to leave partway through the date. There are more little things like this, that aren't hard to do, but will help keep things from going sideways.

The safest bet is to offer to pay your portion, the guy won't let you on a first date, but that's the safe bet. He'll definitely pay. Nothing wrong with that performative offer to pay from you. Do let him pay for you for sure on a first date (if he tries to, which he will)

So it's very normal to be nervous.

But... this seemed sorta not quite right to me:

"We've barely chatted about anything significant. I don't know much about him other than the basics. He's an enigma to me which scares me."

So it's alright that your talks aren't significant. But you should definitely feel like you're getting to know him a bit. At the very least to learn what kind of person he is (if he's funny for example) even if the actual topic of conversation isn't significant.

You feeling that he's an enigma scares me too.

So why did you decide to go on a date with this guy? Just liked his looks? Something about his profile? What made you choose this guy to go out with. Often, if the messaging conversation isn't going well, a girl will choose not to go out with that guy, for fear that face-to-face conversation will be just as lackluster. That's not a rule or anything. It just seems like there isn't chemistry (at least not yet) that's prompting you to go out with this guy. What do you like about him?

🙂

Blunky · Accepted Answer

Just ask the basic stuff like:

What do they do for work or school and do they like it (career-minded or indecisive? do they support themselves?)
What do they do during their free time (hobbies? do they even have any? something they're passionate about?)
Do they have family and are they close with them (close relationships?)

Be prepared to answer these questions yourself so that if you want, you can go in depth on them. Pay attention to how they respond to questions and behave in general. You can learn a lot by watching the way people answer these questions like if they're comfortable in their own skin or not. You really don't know what you're getting when meeting people from online dating. He may very well be a catfish or an alien wanting to infiltrate and destroy the human race from within. Just have conversations like you would normally to gauge whether or not you two vibe or not.

natured · Accepted Answer

So first of all, please be careful with these dating apps, you should know that not everyone is there too meet people and a potential relationship... Most of them want pretty much just one thing and I let you do the Math here.
Second, I get it, you're new to the dating scene but remember no matter what no matter with who, BE HONEST and be yourself. If you are open about yourself you will reflect that energy and people are going to be more willing to be open to you as well.
Let everything flow naturally, talk about how this is new to you, and why, and how you got to college, and so on... don't hide things, be proud of who you are...
I hope you're going to have a blast but PLEASE make sure you chat to the people on those apps MORE to find out their true intentions... I just don't trust them

FreyaRed · Accepted Answer

"I want to impress him"
It will very likely go wrong. Just take it easy and rather as entertainment. You should figure out what is his main goal while dating you, is it sex, is it relationship or is it just fun while going out together.

ohsheeT · Answer

Well I think your in good hands. Because you sound fun And it sounds like you have a great sense of humor
and I think you can read The situation on what's happening And either change it or make it work
you sound like your very down to earth a beautiful heart I wouldn't try to impress him you should just be you because that the best part of you and if it doesn't work out you can always come back here lol. Good luck your going to be fine

Shiprex · Answer

Dating apps aren't known for their romantic outcomes but hook ups are their main thing. SO don't be surprised if this guy wants to get physical quickly.

As for the date set yourself a time frame for the whole thing to be over and avoid being pressed into doing something or going somewhere private with him. Be honest and polite and try to be relaxed and yourself. Have some questions and things to talk about as well as things you want to know about him.
What are his aspirations, where does he work, how long, why he does this job etc. There are also things like hobbies and activities, places they've been to and just things they've done in life to discover. Family state and goals could be something to talk about too.

Good luck!

serious · Answer

Well, it should not matter if he is of the serious type or not. What should matter is if there is compatibility in thought process, having similar likes and dislikes etc. If there are more similarities, more common ground as compared to differences then there is a good chance things will work out well.

I think you should see if he is genuine, authentic, mature and if he has good manners or not. Then you can decide accordingly.

NicholasRedone · Answer

So you're 30 or 35 going in this first dating world? Lady I hope you manage to have a good boyfriend and a good time before your body ages further and you don't get to experience the joy of making love lol before 35 or before menopause strikes and thinks get dryer, wrinkled

chrissykerdock · Answer

he'll take you somewhere but onthe way back he'll find somewhere to park he'll start kissing you then he;ll take out his cock and want fellatio after he cums in your mouth he'll say we should do this again

exitseven · Answer

Just be friendly and honest. Do not expect too much but do not overcompensate for your inexperience. If it does not work out do not give up. Remember , everybody has to start somewhere.

glennos89 · Answer

Always offer to payat least half the bill... Real men will appreciate your willingness to pay but respectfully decline the offer

Anonymous · Answer

I would try to just relax and be yourself! I personally always offer to pay my part especially when just getting to know someone!

Anonymous · Answer

I'm even older than you, and I've never been on a date before, never had a kiss, still a virgin.

LiamS95 · Answer

If you want to practice some dating scenarios you can dm me and I'm willing to help.

jahaims · Answer

Just go be a person and don't over think

Jennz6 · Answer

Sex.

I'm in my 30s and I've never been on a date before. What should I expect?

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