When you’ve been single for a few years, you tend to be that person. You know, the one that your friends always want to set up. The one they turn to for advice when they themselves are entering the dating world. The one they cut off after too many glasses of sangria at a wedding. The one they assume spend every Friday night out at a hot new spot, when in reality you’re at home doing laundry and Facetime-ing with your parents. That’s me!

I’ve been lucky to have gone out with some pretty awesome guys, and I have had my share of funny dating stories: going out on a date with caramel stuck in my hair, getting asked out by a random/hot/young stranger while eating a kale salad, going out with someone who is allergic to chocolate (obviously that did not work out), or someone who looked like Ben Affleck (from the nose down), and another guy who looked like Jeremy Renner WITH GLASSES (oh yes).

So I think by now, with all these years of dating experience, my love for restaurants, and my innate obsession with making lists, I can give you some semi-professional-ish advice… on The Best Date Night Spots in Boston, and What To Order when you’re there.

Here are five of my favorite date spots, for different dating scenarios, and my suggestions on what to get:

Brunch: The Painted Burro, Somerville

Order: iced coffee horchata or michelada + crab cake benedict

I love The Painted Burro for brunch. It’s bright and colorful, you have the option to drink margaritas and many different kinds of tequila, and you get free nachos and salsa (even for brunch). This combination is sure to put you and your date in a good mood. Order the iced coffee horchata (an iced Mexican drink made with ground almonds, rice, vanilla, and cinammon – transformed into a morning beverage with coffee) and your date is already off to a sweet start! Or you might enjoy the michelada more (a Mexican cocktail made with beer, lime juice, hot sauce, and other seasonings) if you’re the kinda gal or guy who likes alcohol early in the day. And I suggest the crab cake benedict because crab cake. Benedict.

Fancy or Special Occasion: O Ya, Leather District/Waterfront

Order: foie gras nigiri

O Ya is the best Japanese restaurant in town (and also the most expensive). I had my most extravagant meal there a few years ago and loved it. After going to Japan earlier this year, I have newfound respect for sushi (it really is like a work of art) and the food at O Ya is pretty impeccable (and did I mention expensive?) If you’re into sushi, too, then you probably already have your favorites, which you should order. But may I suggest the foie gras nigiri? It comes with a balsamic chocolate kabayaki, claudio corallo raisin cocoa pulp, and a sip of aged sake. So really, you get a good deal for ordering this because you also get sake.

Foodie Date: Craigie on Main, Central Square

Order: the burger (only available at the bar)

I know a lot of people hate on the word “foodie” but Craigie on Main is a great spot for foodies. The food is local, seasonal, organic, farm-to-table, nose-to-tail eating. It’s a little bit fancy, a little bit country. I’ve been there for brunch, bar snacks, dinner, and while I liked everything I’ve had, my top choice is the burger (and after that, the crispy pig tails). The iconic burger is definitely one of the best in the city. Salty, juicy, and bursting with umami flavors; the patty contains different cuts of beef, bone marrow, and dehydrated miso. I also like the tasting menus at Craigie, and the Chef’s Whim on Sundays (a 6-course surprise menu for $57) is a fun way to try special dishes that may not be on the regular menu.

Fun: Lulu’s Allston, Allston

Order: Mexican Cheetos

It’s fun! It’s kitschy! It’s in Allston! Maybe the exclamation points aren’t enough to make you head over to Allston but these Mexican cheetos with hot salsa should. Who doesnt’t like Cheetos? Lulu’s Allston is a good place for a fun date. The new bistro serves casual comfort food – like you’re eating “drunk food,” says The Boston Globe, and the menu really is filled with stuff that’s perfect for curing hangovers. The bar offers over 50 beers, cocktails (like the sangria pictured above), and other beertails (which is exactly what you think it is) so if you need liquid courage (or beer goggles), you’ll be all set.

Romantic: Harvest, Harvard Square

Order: Taza Chocolate Cremeux

A date night round-up wouldn’t be complete without a nice place with a swoon-worthy chocolate dessert. Harvest is perfect for a romantic night out. The place feels very refined, but not at all stuffy. To get there, you have to walk through a charming little walkway in Harvard Square, and if the weather is good, you can sit outside at the lovely patio. You can’t go wrong with the classic American cuisine, and make sure you save room for dessert. The best is the Taza Chocolate Cremeux – intensely fudgy, with a thick caramel filling, served with crunchy granola, creamy mascarpone, and flakes of sea salt. Food may be the way to a man’s heart, and I think chocolate is the way’s to a woman’s, but both genders will agree on this sexy dessert. Share this with your date!

If you see me at any of these spots on a date, please remind me that I shouldn’t order tequila shots (at least not on the first date). What’s your favorite date spot?