First date ideas aren’t easy to conjure up when your heart is racing and you’re still wondering just a little about why they actually said they’d go. You’re amazing, we know, but it’s still mind blowing that the person of your possible dreams said yes! You don’t just need some regular first date ideas. You need some first date ideas that will help you make a great impression in Boston!

We’re here to help. We scoured the web, harried our friends, called upon Emma’s enormous body of knowledge (Emma, I said your knowledge is huge, not your body. Seriously. You get first dates with knowledge that big? Ha!) to give you the best first date ideas in Boston.

Provided neither of you is sketchy and you’ve had at least a few minutes of conversation prior, meeting up for dinner can be a nice first date idea. Boston has loads of great places to go on a first date and we’ve selected 10 places that are interesting, fun, and will impress at least in a quirky way.

1. Kaze Shabu Shabu – Boiling broth on a table makes for an interesting meal experience!
2. Cuchi Cuchi - Oh, Tapas!
3. Pho Republique – Amazing Vietnamese
4. Meyers & Chang – Asian Fusion
5. Addis Red Sea – Ethiopian
6. Finale – Dessert’s a win!
7. Tapeo – Tapas is an easy first date idea and delicious variety!
8. Bacco – Italiano! Taste Boston’s North End in style.
9. Mike’s Pastry – Pair with with coffee after Bacco or get sugared up directly!
10. L’espalier – French. Oh, the French! Emma, this is for you.

If you’re broke or full, walking along the minuteman trail, finding a quiet spot along the Charles, or splashing in fountains atop the Big Dig all heap together as some great first date ideas to try out in Boston.

If you’re a local and would like to add some insight or even more ideas, please check in with a comment! Thanks!

Image: Zitona

by Jane Wonder

Who pays on the first date? I’ll tell you.

On a first date technically the person who asked should really pay. For me, this will always mean the guy because I will wait for him to ask. Honestly though, I’d prefer for the man to step up no matter what.

Which is not to say I expect that or don’t offer or won’t pay in the future. Every good female dater knows exactly how to handle this. In case you don’t know, let me explain…

The check comes. The woman should automatically reach for her purse and say something like “Let me help you with that.” This gives the man options. If he didn’t intend to pay the entire check, he can accept the offer without losing face or having to ask for money. If he did intend to pay, he can say “No, I’ve got this one.” The woman should then ask ONCE (and only once ladies) “Are you sure?” If he waffles at all, offer money. This next bit is important now. If he says he’s sure, look him directly in the eye and thank him for your meal. Read the full story

What dating advice would you give to a guy who’s so shy that he never gets past “hello, my name is…” with a girl? Nicholas recently wrote in with this question:

Seth,
I recently approached a girl that I’ve been crushing on for the past month or so. I was really nervous and out of my element. I’m sure she picked up on it but I’m not sure if she was in to me. We have exchanged looks, and recently names, for a while now but she still remains a mystery. We work in the same mall and I think she’s about my age (23). What do I do and more importantly how do I know if I should keep talking to her? I’m American and she’s Israeli by the way. Thanks!

Nicholas

Hi Nicholas!

I’m sure others will have more to add but here’s my $.02 worth of dating advice:

You’ve barely talked to this girl and yet you’re asking if it’s time to give up? Come on, Nicholas! You can’t give up yet!

Three quick things about relationships: Read the full story

Sometimes, no matter how well a date seems to go, the last you’ll hear of her voice are the words “please leave a message”. You had fun, but she doesn’t call back. You enjoyed your meal or activity, but she doesn’t call back. She even said she liked you, but she doesn’t call back.

Why is that?

Maria and I went out for sushi then drinks at a bar overlooking the river. The weather was perfect. Our conversation was a mix of questions and comments, silence and laughter. Everything seemed to go well. 

When I dropped her off at her house, she even said “I had a really nice time. Call me!”. 

So I did. And she never called me back. Why?

The answer is agonizingly simple: Read the full story