Reykjavík is small enough that you can walk between most date neighborhoods in twenty minutes, but each one still has its own personality. Picking the right street matters more than picking the right restaurant, because if the first place is wrong you can drift two blocks and try again.
101 Reykjavík: Laugavegur and Skólavörðustígur
The postcode 101 is the obvious answer and it is obvious for a reason. Skólavörðustígur, the rainbow-painted street that climbs toward Hallgrímskirkja, is the best opening move in the city. Start at Reykjavík Roasters on Kárastígur for a flat white, then walk uphill slowly. There are wool shops, ceramics studios, and the Handknitting Association if you want a low-pressure browse. If conversation is going well, keep going to the church steps and look out over the colored roofs toward Esja.
Laugavegur, the main shopping street that runs parallel, is louder and better for a second hour. Drop into Mál og Menning, the bookshop with a cafe upstairs, when you need to sit down without committing to dinner.
Grandi: the old harbor
Grandi used to be fish processing plants and now it is bakeries, breweries, and the Marshall House art space. It is a fifteen-minute walk west from downtown along the waterfront and the walk itself is half the date. Bryggjan Brugghús has a long bar facing the boats. Valdís does ice cream year-round, and yes, Icelanders eat ice cream in February. If you want something more substantial, Matur og Drykkur does proper Icelandic food in a former salt fish factory.
Grandi works because it gives you an excuse to keep moving. You can wander into Whales of Iceland or the Saga Museum if there is an awkward silence, but mostly you just walk and look at fishing boats.
Vesturbær: the residential west side
If the person you are meeting lives here, this is where they want to go. Vesturbær is quiet, full of small wooden houses, and centered on the Vesturbæjarlaug swimming pool. Kaffihús Vesturbæjar, on the corner across from the pool, is where locals actually read the paper on a Saturday morning. It is not a tourist spot and it does not try to be one. Take a date there if you want to signal that you live here, or that you would like to.
Hlemmur and the east end of Laugavegur
Hlemmur Mathöll, the food hall in the old bus terminal, is the lazy person's perfect first date. Six or seven food stalls, shared tables, beer and wine, and you can graze for an hour without committing. Skál does small plates with Icelandic ingredients, Flatey makes good Neapolitan pizza, and there is a fish counter if your date is into that. The crowd is mixed, the noise level is forgiving, and nobody is watching you.
From Hlemmur you can walk five minutes to Klambratún, the park behind the Kjarvalsstaðir art museum, and keep talking outside.
Seltjarnarnes: for date number three
This is not really a first-date neighborhood but it is worth knowing about. Seltjarnarnes is the peninsula at the western tip of the city, past Vesturbær, where the road ends at a small lighthouse called Grótta. You can only walk out there at low tide. Save it for when you already like each other and want a forty-minute walk with the wind in your face. It does not work as a meet-cute, but it works as a confirmation.
How to choose
If it is your first time meeting, pick Skólavörðustígur. The hill gives you something to do, the shops give you something to talk about, and the church at the top gives you a natural turnaround point. If you already know each other a little, Grandi is more interesting. If you want to feel like you live here rather than visit, go to Vesturbæjarlaug and Kaffihús Vesturbæjar afterward. Reykjavík rewards walking, so plan a route, not a reservation.