Put it in the story
If you (the author) are debating how to proceed, it might be an opportunity to put that same 'conflict' into your story. Transfer your hesitation, and the whole "What if I…" debate onto your character. We'll get to see how the character is 'not aggressive' and 'not outgoing', and we'll know he must get past this indecision to get what he wants.
This is all good character-building stuff that makes us feel sympathy – just, don't make it too easy. Your inexperienced protagonist wants to take the easiest path forward (least risk). At the same time, they have been imagining these wonderful dates and intimate conversations, just as you have. There is a lot of anticipation by the character, so the reader will feel it too. We understand what's at stake.
As writer, your job is to put some obstacles in the way, and in this case it's easy to imagine how someone who is shy and 'not aggressive' would make a mistake. Let's say he decides a walk in the garden is too romantic, and getting a coffee is the safer, less risky first date. When they get to the coffee shop, it's crowded and loud, maybe there is a misunderstanding (she doesn't drink coffee) or somehow everything he'd imagined doesn't go as planned. The date is a disaster until they leave the coffee shop and go for a walk, where it's quiet and they can just talk. It turns out they are in the garden, but it's friendly and comfortable, not 'romantic' as he'd imagined….
The point is, once you introduce the conflict, it will need to pay off somehow. The first date becomes more interesting because there are expectations from the protagonist, but he creates his own conflict through inexperience. As author you get to have your cake and eat it too. You can present the various ideas you are debating through the character, and the character will pick the option that seems easiest, which is almost always the wrong choice (up until the end of the story when they are doing all the right things and have the right expectations).