First date- Her b'day is at midnight. What to do?

I met a woman online (not in person yet) that I have a first date with Saturday night. We’ve been talking online for a while and finally on the phone this past week. I really like her a lot so far and have a really good feeling about her.

I’m taking her to Williamsburg, Brooklyn (she’s never been there before) and we’re going to start off at a nice little romantic Italian restaurant. Then we’re going to walk around and I’m going to show her my favorite places.

Sunday is her birthday which means it will be her birthday at midnight. I was thinking during dinner I would give her a toast with some wine and she’ll probably be happy that I remembered since she only told me when her birthday is once a few weeks ago.

I’d like to get her a little something, but I don’t want it to be anything too impressive as I don’t want to spook her with an expensive gift on a first date. Any ideas? Is the wine toast a good idea?

I like the wine toast, or you could even do a little Champagne if she likes it. I think the crux of it is that you want to convey that you remember that it was her birthday and wanted to acknowledge it, but you don’t want to do anything over the top or too personal since it’s your first date.

Make sure she likes whatever you’re getting. Maybe ask her what her favorite drink is, and then get a slightly higher quality one? Like if she’s into wine/Champagne, buy the fancy version, not the standard one. Or if she prefers a cocktail, get her the name-brand liquor. That kind of thing.

If she’s not a drinker, maybe dessert?

My vote would be for the wine toast and nothing more. I think that’s the right amount of attention to pay to the event on a first date, and more than that would inevitably run some risk of seeming like awkward overkill.

Exactly, Athena. I don’t want to do anything over the top or too personal, but not because I mind spending the money, I just don’t want her thinking I’m a weirdo for doing so or making her feel uncomfortable.

I already plan on getting her desert and the best of everything while we’re out. I like the champagne idea. Maybe I can slip in asking her if she likes it on the ride there.

I don’t know why, but I feel a little funny about not giving her a gift she can rake home with her even though I’ll be paying for the date. Any ideas for something nice that’s not too over the top?

Agreed. Do the toast, skip the gift.

This probably won’t be a popular answer, because I’m a sappy romantic, and we’re a dying breed on this cynical internet world. But I’d play the single not-red rose on her plate. As in, call the restaurant and ask if they’d put a flower on her plate if you brought it to them earlier in the day. (If it’s a nice place, they’ll probably provide a flower for you, for that matter.)

But really…judgement call. If she seems the sentimental type, it would probably go over well. If she’s the kind to read too much into things, though, maybe it might be scary.

I like that idea a lot, WhyNot. She absolutely seems like the sentimental type and I think she’s love that. I’m a bit far from Williamsburg so getting there earlier in the day isn’t much of an option. I’ll call the restaurant tomorrow and ask if they can do the flower or have any ideas. Thanks.

You could do a small box of nice chocolates.

Ignore every suggestion but this one.

I concur.

A small gift or WhyNot’s flower thing is too much. If this were your 3rd date and you were really into her, those are great ideas, but you haven’t even met this woman yet.

Okay, I’m back to just the toast and seeing if she likes champagne. Thanks guys.

Yeah, I did flowers for my wife on the third date, but I had an excuse that it was her birthday, and it was our third date. On a first date? No.

Drinks or something low-key are appropriate, though.

That said, there are women out there who like the no-holds barred, non-conventional, not-by-the-rules approach. There’s no one-size-fits-all solution, but you can’t go wrong with keeping it low-key and just buying a champagne toast or something similar. Dating advice on the Dope tends to be conservative. From my perspective, it tends to be very good middle-of-the-road advice, but if you want to attract, say, more off-beat personalities or a specific niche of personalities, it might not be the best.

This is good advice.

The problem with even mildly grand gestures on a first date is that the subject in questions knows that you don’t know them very well, which means the gesture isn’t really about them as a person, but rather a fairly generic thing you’d do for any woman who happened to be sitting in front of you at the moment. It’s not flattering or romantic to be treated to something that was planned with “generic woman” in mind.

Get to know each other and have some fun on the first date, and save the special stuff for when you actually do have reason to believe she is special.

Another vote for low-key, no gifts or flowers. Back when I was internet dating, I wouldn’t even plan a romantic meal for a first meeting- that’s too much pressure and gets too awkward. IMO, a meeting should be quick and simple, and any real “dates”, if any, would be planned from there. But since you already have this planned, at least try to keep it low-key.

This but in the toast tell her that you want to be the first to wish her a happy birthday.

Trust me on this.

^ I like that!

Extra key to your house and car is right out then, I’m supposing?

I like flowers - I’d go with that, but a simple, fun bouquet - like a few gerberas or something, not roses. Flowers don’t have to be overly romantic - I’d easily give flowers for a friend’s birthday. The single rose seems too romantic / “Bachelor” cheesy for me. JMHO.

Another vote for this. Anything more is gonna look a little skeevy, or something.

Let us know how it went.

The only thing I can thing of, beyond the toast (great idea) is if any of the places you will be visiting are kinda touristy, I would think that a little knickknack, as a funny momento, could be ok. Say you found yourselves laughing over a cheesy refrigerator magnet, or something on that scale.