Should I take him on a date? (For the third)?

[Anonymous]

So I went on a couple dates with a successful guy, he is 7.5 years older than me, I am in my mid-20’s he is in his early 30’s, he has spent a lot on the first couple of dates and a couple of my male friends said I should take him on a third? Like plan a picnic or something? Is that just going to turn him off and seem like I’m chasing? They said successful guys like when a girl plans a date so they don’t seem after their money. They also said since I’m not doing sexual things aka 3rd base and home-run I have to make up for it by taking him on a date so I’m giving back?

[HollyK21]

So I read this and your comments to others and here’s my take. Relationships of any kind take mutual effort, not one person traveling both lengths of a two-way road. He initiates texts, you initiate texts. He makes effort to go see you, you do the same in return. That’s how you keep a healthy balance so the other person doesn’t feel like they’re chasing or the only one trying.


It would absolutely be fine to ask him out on a date, especially if he’s been the one doing so. To be fair, I know some men prefer you not pay, I know my partner will verbally protest when I try pulling my card out lol. Of course, not every guy is like that, so if you offer and he accepts then go for it.


I’m not sure paying for a date is the real issue here though. You said elsewhere that you basically feel like he’s talking to you less and you’re afraid of chasing him off. In which case I’d say if he’s decided you aren’t a good fit, then don’t worry so much about that and let him go. You two are still pretty new to one another and this early juncture of time is meant for you both to decide if this is worth pursuing. Sometime no matter how you play your cards it inevitably isn’t meant to be, so prepare yourself for that beforehand so you’re not looking for a last-ditch effort to keep him.


Lastly, doing your part is not chasing.

[Asker]

Great thank you! He still messaged first after the second date but has not brought up a third. I’d feel awkward to pay on a date so I thought about picking him up and planning a beach night picnic with desserts, string lights, board games, and a football? (This would be for the third)

[HollyK21]

Sure! I think that would be fun and thoughtful. Have you been in good communication? I saw elsewhere you said it hasn’t been a lot of conversations as of late..

[WhyohWhy69]

I think you’re an incel, tbh. You sound like another anon female who got busted being a guy. Lol.

[Billlewis]

Yes, ma'am, I just started following you and I'd like to invite you to follow me, as well, if that's alright. Thank you very much.

[Staximus]

I don't see how that's going to turn him off and make you seem like you're chasing. Where do you come up with this crap? Don't play stupid games. If you want to see him again and he wants to see you again, I'm sure he would like it if you suggested to go somewhere and do something.

[Staximus]

Young people these days have problems being sincere

[Asker]

Okay thank you! I’m so confused because my whole life I’ve been told not to chase. It’s been 3 days since the last date and he hasn’t asked for a third yet but he texted me after the date. So my friend said to ask him on a date to seem like a sweetheart? I was thinking doing a beach night picnic with desserts I made, bring a speaker with music, some strings lights, and a football? He said I should do this since on the last date he spent like $500 at a steakhouse

[Asker]

Although I’m worried cause he hasn’t been talking as much since before the second date so I don't know if he’s just not interested anymore

[Staximus]

I don't see why he wouldn't like that plan. Do what you feel like doing and don't worry about what anybody tells you to do. I don't know why you would bring a football to the beach at night, though haha

[Asker]

For a fun activity? Am I better off with a board game?

[boggboss]

I dont see why it would be a issue with u planing a date confuses me how women showing effort is seen as a negative

[Asker]

I’m so confused because everyone says not to chase and never message first and if he wanted to he would. Also that if he really likes you he’ll reach out. Another one is men like to chase so if you chase back he starts liking you less but then someone said stop listening to single women.

[boggboss]

U planning a single date sending a single message wouldn't be a issue if u think women know what men want over men saying what they would find attractive then I guess continue to listen to them and do nothing but hope he stays attracted whilst u put no effort in and hope someone that values him more don't show up

[Asker]

Yeah that’s what my male friends were saying thanks for the opinion he was saying I’d look like a sweetheart. Also, this guy talks to his mom a ton and my friend said because he talks to his mom a lot he’d mention I took him out to his mom, and it’d make me look good like I’m taking care of him and she’d like that. His mom also said his ex wouldn’t make a good partner but I don't know what she did. I was thinking a beach night picnic with desserts I baked, a speaker with music, strings lights, and a football? Would a 32-year-old man like that? I’m 24 by the way

[boggboss]

Its pretty romantic I wouldn't see why he wouldn't

[Asker]

Okay thank you great, but is the 3rd date too soon? He probably spent like $150 first date $300-500 second date so my friends said I should give back in that way. Should I just say I have a surprised for him and I’m picking him up?

[boggboss]

I think simply setting up the date should be fine

[Asker]

Okay great thanks! but I’m a bit worried cause he hasn’t been messaging as much since after the second date but he texted first after though it’s been 3 days but he hasn’t brought up seeing me again😅

[boggboss]

If u have not mbern messaging him why wpuld he message u again

[Asker]

I texted him first yesterday and he replied but he usually texts more? Last text was “that’s great!” so my friend said to reply next day and bring up taking him on a date?

[Asker]

I’m just confused cause he was messaging a lot more before

[boggboss]

Maybe u waited too late to show intrest

[Billlewis]

Sure. Why not?

[Asker]

It’s confusing because everyone says not to chase and he’ll like you less but the men on here are saying different now

[Billlewis]

You'll never know what's on his mind unless you ask.

[Leititjt]

No don’t chase men