Episode 659 · April 21, 2025 · 18 min
10 Gangster Date Ideas for The Second Date and Beyond
About this episode
First dates are easy, quick, and simple — coffee or lunch just to break the ice and get to know each other.
The challenge comes with the second, third, and fourth dates, where a coffee meet doesn't cut it anymore.
Fortunately, Mark and some of his closest female friends have a near-infinite well of fantastic ideas for subsequent dates that 99.9% of men have no idea about. They've put together a list of unique and interesting date ideas guaranteed to spark intrigue in any woman you meet.
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Some of these that I list may be better for a third date, a fourth date, a fifth date, but we as men are responsible to plan the dates. Not always, but about 90% of the time. Once in a while, you can defer to her and say, hey, plan something for us. In that case, the date is in her court. But usually, since we are the man, we have to lead. When you lead, women get more attracted to you. Welcome to the Unapologetic Man Podcast. The only podcast that's all about self-improvement, confidence, success, women, and being a man without making any apologies for it.
What is up, boys? Thank you for tuning in to another episode of the UMP. I really appreciate you. And today, guys, we are going to talk about 10 unique date ideas for the second date and beyond, beyond, beyond. And these ones were actually given to you by my three girlfriends, Ashley, Alicia, and Lindsay. If you're listening, I super appreciate it. You guys helped me out quite a bit to create these 10. And boys, I always deliver. I'm going to actually give you 16 date ideas that these chicks were fucking like hens in the hen house, boys.
They were like, oh, we have so many ideas. And I was like, oh, my hell. Just get it over with, man. Stop your yapping. Tell me what the fuck they are. And I wrote them down. And it was funny because in my last episode, if you listen to it, the signs that a girl will give if she wants to have sex with you, I listed them out incorrectly at the end of the show. And I was going to have Liam try to edit out all that shit.
And I was like, ah, screw it. Just leave it in. But I'm like, number two, da, da, da, da, da. Number six, da, da, da, da, da. Number nine, da, da, da, da. Number four. And I'm like, dude, what were you thinking? And what happened is I listed them all out before the show started. And I wanted to rearrange them. But oftentimes when I'm about to do a podcast, it's a little bit like taking a piss. Like I feel like I have to get it out.
I feel like I have to talk now. Otherwise, I'm going to lose it. So I rearranged them, but I didn't change the numbers. So as I was reading them back to you guys, I got it all messed up. It was a funny mistake. I just left it in. It is what it is. But on this one, I actually have 16. And I did take the time to number them one through 16. Before we jump into the content, gentlemen, want to ask you yet again to help me out with my perks program.
I am giving a ton of different programs, a ton of different training in order for you to simply tell your friends about it, post about it on Facebook, post about it on a forum such as Reddit, a seduction forum, or whatever it is that you can do for me. I have The Conversation Sniper, Three Texts to Build Massive Attraction to Women, Guide to the Female Orgasm. You know she's lying, right? As well as a bunch of masterclasses, templates, what to text girls, what to message girls on the dating apps, as well as a bunch of NLP stuff.
Just a ton of high value content that I want to give to you if you can help me out. Why aren't you fluffing my scruff, bro? I'm fluffing your scruff. I gave you, what is it, like 650 episodes now and you haven't fluffed my scruff? Fluff a scruff, bro. Help a dude out. Tell your friends about it. This is a good podcast and other people need to find it. So once you've done so, click the link below. It's called the Perks Program. Look at all the perks and see, okay, I want to do this for this guy.
Then what you're going to do is you're going to email me after you do said thing and I'm going to send you all the content in addition to you getting all the content, you're going to get enrolled into a drawing to come enter my three-month coaching program. That's going to take place in June. So go check that out right now. Help a brother out. Fluff that scruff because when I scratch your back, you're going to scratch my balls. That's the way things work. The norm of reciprocity, brothers.
If you feel like I've given you good value, could you please help a brother out and give me value back? I'd super appreciate that. The best thing you can do for me is to tell your friends about it. All right, boys, let's get into it. Now, the first eight, in my opinion, kind of all go together. So I'm going to list them off real quickly. But these are second date and beyond activities. So some of these that I list may be better for a third date, a fourth date, a fifth date.
But we as men are responsible to plan the dates. Not always, but about 90% of the time. Once in a while, you can defer to her and say, hey, plan something for us. Or perhaps she volunteers to make you dinner. In that case, the date is in her court. But usually, since we are the man and we are the masculine role, we have to lead. When you lead, women get more attracted to you. Did you guys know that you and I both create, and this is fucking crazy, 12 million sperm per hour in our ball sacks?
You are a man, gentlemen, so it's your job to lead that girl, because those sperm want to get out of there. And in order for them to get out of there, you have to lead the girl. Don't let your dick be so dry. It's going to audition for the next movie of Dune. When you execute these 16 date ideas, you're going to have a higher chance of having sex with her. And stay tuned until the end, because my best idea, I'm saving for the last one. I have done this so many times, and it has absolutely worked like gangbusters.
That's going to be the last one. I'm saving it until the end. So number one through number eight are the following. First of all, a trampoline park, indoor rock climbing, top golf, miniature golf, go-karts, bowling, arcade, or shooting pool, as well as ping pong, table tennis, trying to throw a dart up her butt, and seeing how far she can launch a ping pong ball out of her vagina. These are all things that you guys can do together. Obviously, the last two were jokes. But what I would always do is, say, for example, take her to miniature golf.
I would always bet her something. I would be like, all right, I bet you anything I'm going to kick your ass on today's game. If I do, you have to buy dinner. Or if I do, you owe me a massage. Or you owe me some epic scratchies on my arms, because I love scratchies. Something where you guys can get physical. Now, obviously, this is second date and beyond. This could be the sixth date, for all we know, where you would barter about a massage or something like that.
But if you guys haven't been physical yet, then maybe you make it something else. You always adjust based on where you're at with the girl in the relationship, her comfort level, how far you guys have physically ascended. And you make a fun bet that whoever wins gets to win that certain thing. I do this with girls all the time, especially when they ask me to buy them a drink. If you're talking to a girl in the nightclub and she asks you to buy her a drink, the best thing you can say is, yeah, for sure.
But I'll tell you what, let's play a little game. We're going to shoot lemon seeds. And whoever wins gets the drink bought for them. Deal. And she says, deal. Then you go over to the bar. You grab a lemon. Each of you gets a lemon seed between your fingers and you shoot it by pressing your fingers together really tightly. Whoever's seed goes further gets the drink bought for them. That's the way to handle it when a girl asks you to buy her a drink. So having these little competitions with girls, really powerful stuff.
All right. The next one, boys. These are the ones that my girlfriends thought of. A lot of them are pretty good. A few of them. I'm going to be honest. I was like, that's lame. That's like way too much work for a second date or even a fifth date. I'm a lazy motherfucker. That's why my one that I'm going to tell you at the end is one of the best. But usually what I do is I do those ones I just mentioned. I like to do activities on the second or third date.
Or if I feel like I'm going to have sex, just be like, yo, come on over and we'll Netflix and chill. Or as my apron says that I barbecue with, Netflix and grill. Because when you get the girl over and you guys have like pizza and you just watch Netflix or whatever, you're probably going to have sex. But these are some cute ideas, especially if you want to spice it up. Brought to you by Lindsay, Alicia, and Ashley. The freaking sewing circle, bro, that delivers every single time.
All right. Number nine, thrift store challenge. Here's their thoughts. This is so lame, but I guess it would work. All right. Each of you has 20 bucks and you go into the thrift store and you buy the other person's outfit. Then you wear the outfits to dinner. I can honestly see this working where you get her dressed up like a freaking canyon mule. She gets you dressed up like a sea donkey. You guys look ridiculous together and you go out and you eat a meal. I think that would work pretty well.
Pretty charming. Next one is food crawl. And this is actually something I suggest on the first date where you go to multiple spots. But in this case, all you guys do is go grab appetizers and drinks and then you lead it up to dessert. And this is really good to do in like cities like Denver. I can see this working in Boulder, Fort Collins, or if you like live in New York, LA, Austin, wherever you happen to be, where there's a lot of different restaurants where you can sample the food and go on a little food crawl.
Girls love this shit. Doesn't surprise me that these girls thought of these ideas right here, but we got to give women what they want, lead them to where they want to be led. So if this is what hot girls are coming up with, and believe me, boys, these girls are fucking hot and they know what they want, you would be smart to listen because these are some good tips. The next one is a sunset scooter ride. I can definitely see myself doing this where in big cities, I don't know where you live, but in my city of Denver, you can rent scooters.
I think they're run by Uber or something like that, but you just slap a credit card in and you can rent scooters and you guys can go on a sunset scooter ride or maybe a sunset rent bicycle ride that most cities have or something similar. Maybe you could take your skateboarding or I really like one wheels. It's that electric skateboard that just has like one wheel and you lean on it like a segue and it goes. I love my one wheel. That thing is so sick and I actually have two of them.
So if I were to go on a date with the girl, I could be like, hey, let me teach you to one wheel or maybe she one wheels herself and we can go cruising around. That would work really well. The next one, and oh my God, this has female juice written all over it, man. These chicks sprayed their female hormones all over this one. A mystery date. Tell her nothing other than just dress casual but cute and take her to an escape room, a comedy show or something unexpected.
The mystery itself is the attraction, says Lindsay. God, boys, they got so pumped on this. And by the way, when you join us in our three-month coaching program, these are the same three chicks that go through your pictures and tell you which ones to use in which order. That is a service that I reserve for my clients. And they come over and it's like herding cats. And I'm like, all right, girls, come on, go through Brian's pictures. And they're like, oh, he's cute. And like, put this one first and this one second.
They tell you the order, boys. Because while taking dating advice from females is often not advisable because you would never ask a fish how to catch a fish, I will say that in certain aspects, female advice when it comes to this stuff is valuable, particularly when choosing your pictures. In my opinion, the only female dating coach that's worth her salt is Marnie from the Wing Girl Method. She's an absolute champion. Definitely check her out. But other than that, bro, you don't ask a fish how to catch a fish.
Just my opinion. Next one. And this too was sprayed all over the face with estrogen. Wine and paint at home. Are you fucking kidding me? This is so female right here. Okay. You get wine and you guys paint each other's portraits. Again, it's a lot of work in my opinion, but maybe this is a good date idea for like after you've been hitting it for a while and you guys are locked in. Wine and paint at home. You guys paint each other. You laugh. And then you fall down in a puddle of paint and make sweet, sweet love until the sun rises.
Next one, speaking of the sun, is a sunset hike with a thermos or coffee or wine where you guys hike somewhere and then you get to a point and then you can have coffee or you can have wine and maybe some appetizers. I've done this many times myself. It's a cheap date. It's fun. It's active. You guys get to exercise together. And sometimes too, like especially on the second date, it's good to do an activity because it doesn't put so much pressure on you continuing the conversation.
It takes a little bit of that get to know each other burden off both your shoulders where you guys can do an activity and have a good time. Then you push her off the cliff. She hangs on by a fingernail and then you save her life. You're getting some sick, dog, bro. That's the Mark Singh pusher then saver technique, which gets you laid every day of the week and twice on Sunday. Next one is cook together and role play. Pick a dish neither of you have made before.
And pretend you're competing on a cooking show and you say, I'm Gordon Ramsay and you're about to get roasted. These girls, bro, why did I ask them? Literally, boys, why did I do that? I'm fucking with you, ladies. I know you're listening. This was great stuff. You over-delivered as usual, but I'm not going to be like, okay, I'm Gordon Ramsay and I'm judging you. So don't make a mistake and then yell at her for it. Man, some of these are cheesy. Now, number 16, boys, this is what I do.
This is the pimp method right here. Hot tub. And in the hot tub, you play truth or motherfucking dare. You want to get your dick sucked in a hot tub? Truth or dare, bro. You're going to have your ass cheeks on the side of the hot tub with your legs spread on her shoulders and she's going to be sucking your dick and then this family is going to walk in and you're going to be like, I'm so sorry. And because you're afraid, have you ever had this?
You're afraid you're going to cum. Have you ever been like caught masturbating on your parents and you like start cumming? And by the way, think about that from an anthropological perspective. When we're having sex with a girl, we get startled by perhaps the alpha male or the woman's mate. We cum, therefore, to get our cum inside of her to have a higher chance of procreating. So there you are, dog, in the hot tub, getting that sick duck and you spray cum everywhere as this poor family, this innocent Christian family comes in and you're spraying cum all over the place.
You're a fucking sick bastard. You should be ashamed of yourself. So hot tub and you play truth or dare. For those of you who don't know, truth or dare is pretty simple. You tell the person, all right, I'm going to ask you a question and you either have to tell me the truth or you can ask me to dare you to do something. So this is really good to take things sexual where you ask her, like, how do you like it in bed or you dare her to, like, slip her top down and show you her nipple.
God bless America. This works good in the hot tub. All right. Being it that I prepared this time, unlike my last episode, I actually have them numbered. Let's go over them. Trampoline park. Number two, indoor rock climbing. Number three, top golf. Number four, miniature golf. Five, go-kart, six bowling, seven arcade, eight pool, nine thrift store challenge where you guys get dressed up like a couple of sea donkeys and go to dinner, 10 food crawl, go to a bunch of different places, have appetizers, 11 sunset scooter ride where you rent like a scooter or a bike and you guys go check out the sunset.
Number 12, mystery date. Tell her nothing but take her to an escape room or a comedy show. 13, wine and paint at home. I ain't ever doing that, bro. I'm just being honest. Too much work. 14, sunset hike with the thermos or a coffee. I have done that one. Very successful. 15, cooking together and role-playing. I've cooked with chicks. I don't know about the whole role-playing thing. I mean, maybe I'll play the role of a dude getting laid. That would be a good role-playing scenario in my opinion. And number 16, hot tub where you play truth or dare.
The Mark Singh secret second date challenge works so fucking well. So boys, you have to come up with creative ideas in order to keep the girl entertained and you need to lead her to where she wants to be led. As I said, occasionally she could take the helm and entertain you and that should actually happen because you want to make her work. But for the most part, the first date should definitely be on you. Second date, probably on you. Third date, maybe you guys work on it together.
I think cooking at home is really good or Netflix and pizza because you're probably getting late on the third date. And then fourth date and beyond, you're working some, she's working some, you're working some together. But you need to bring the thunder, bro. You need to entertain these chicks. So these are some really good ideas. And boys, if you feel like I've delivered to you, please reciprocate my kindness. Tell your friends about it. Then email me at coachmarksing at gmail.com and I will send you all those cool perks as well as enroll you in the drawing to come into my three-month coaching program.
A program that guarantees the 10x your results with women, a transformation, not just more information. I've fluffed your scruff, so now it's time for you to fluff my scruff. That's the way it works in the world, boys. I scratch your back, you scratch my balls. It's just how the norm of reciprocity goes down. So I'd super appreciate that. Please do it right now while it's on your mind. Also on that page, that perks program page, you can actually copy a pre-written text that you can send to your friends and then just paste it into your texting app and send it to your friends.
Easy peasy. Then you email me. I send you all that cool stuff and you have a chance to come in my three-month coaching program. Guys, I super appreciate you listening. I draw a podcast on Mondays and Thursdays, so please stay tuned for the next one and I will see you in the next episode.
This transcript was made automatically, so a few words may be off.
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