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Personal qualm with the game, It's kind of annoying how the sms messages will go up in level with you. You don't ever get to feel like you could go step down the the 'weaker' dates and you won't ever really feel like you get to go to the higher sms messages, when winning the easy one can be partial rng. (I almost got softlocked into continual losing because I couldn't add more cards with a lack of money and the easy one would beat me in 5 cards 0.0)
Great game so far though! Just small disappointment that it doesn't feel like you properly grow except through the story, leaving it to feel pretty disconnected.

We hear you and understand that. There isn't any reason why you would need to go on weak-weak dates as you level up. Besides getting a quick power trip, it will feel like a useless as the xp and the money earnt through them won't be worth anyone's time. The easiest date should be fairly easy, if you're having trouble beating them, I think that's to do with your deck build, I wouldn't say it's a 100% guaranteed win all the time but more so like 90%+ win rate.

We've thought about adding a sort of 'endless' battle mode that acts like the boss mode where you start with date level 1 and continually work your way up to higher date levels all in one battle until you run out of lives. This could be a thing that would give one the power trip fantasy that you seem to be desiring.

I guess? It's not so much the power trip, but more so that it feels like the rpg element is taken out for the player. Don't get me wrong, I do like one here and there, but that's not what I'm talking about. 
Like, the game feels like a sandbox game right now (as most games in development do) but this part is controlled for the player. You said it yourself: "It will feel like...". You saying that is fair, but the player may not feel like that, as is their decision and feelings to decide for that. If they don't like the lack of xp and money while not progressing characters' development, they will just move on to the higher levels when they want to. (Just like in any rpg or similar games).

Maybe they want to mindlessly grind with minimal rewards, or maybe they want the challenge. And, to be fair, my deck probably isn't optimized, being 1/3rd of each group and 1 or 2 Bird Cards.

Point being, it feels like the control of the game gets shifted away, instead of being to the player. This leads to an almost bland feeling with minimal gameplay loop. Cause if you allow one to grind for levels, let them actually have in impact in the part that is getting grinded. Otherwise, why have them in the first place?

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I understand what you mean now. I did have a really long comment detailing a lot of things and sharing ideas on why I can or don't think it's a good idea to change, implement, or update the way it's setup at the moment. Most of my worries comes from game performance and the hit it'll take if it's having to RNG and load dozens and dozens of dates every time the player progresses time instead of just 4. And the ease of navigation, how much more of a pain it is to the player if scrolling is added into the mix.

But long story short, the problem is the lack of feeling the impact of the grind itself. When you level, the dates level with you, and that makes the player feel stagnant. In typical adventure RPGs, you progress by physically moving into harder areas and terrain. In Sugar Service, you are limited by a city and even more restricting, the in-game sms page. 

A probable solution I may have is a star progression system and a city zone area system. Each 'page' (these will act like areas or zones of the city) will have 4-5 date opponents. You can earn stars by taking them out successfully. Based on how much health you have left on success, will determine how many stars you earn (how well you did). You can gain 3 or 5 stars (still deciding on the idea). To progress to the next area of the city, you'll have to spend your stars you earned. 

You are free to grind out and max out all the levels but you are also free to get by with the bare minimum needed. For example, in one area, if every opponent has the potential for 5 stars, and there are 4 of them (ascending in levels), you can earn a maximum of 20 stars per area but you'll only be required to spend say 12 stars to proceed to the next area, which then hosts the next 4 harder opponents. Leveling up then going back to easier levels to max out the stars you havent collected so you can unlock harder areas will add to the progression you're looking for.

This may be the way to solve this gripe you have with the RPG, card grinding and how they feel lackluster in progression.