How Can I Flirt on a Train and Not Seem Creepy?

800px-Auto_Train_PlatformQ.  There are a few fine ladies that I have the pleasure of sharing my 45-minute morning train commute with.  Although I have done nothing but steal furtive glances up until this point, I was wondering what you think is the best way to introduce myself and eventually woo them (one at a time of course). – Dr. Love Train

TN-OK: I actually know a couple who met on the New York City subway, so this is not an abstract question.

It’s great that you don’t want to be creepy, or date all these ladies at once (which could also be filed under creepy, depending on your approach).

I think that meeting someone while commuting sounds fantastic; second only to my dream of meeting someone in the grocery store. It is possible, but not simple.

Your approach should take all the basics of good commuting and polite society and just bring them together. You’ll also have to add a dash of bravado to engage a lady directly at some point.

If there is one that catches your fancy without headphones, start there. A friendly smile as she walks by you on the platform is a good place to start. Try it a few times, maybe also a smile on the train as she passes by.

The first time she might not catch it, but if she notices it a few times she might start to smile back. Single ladies notice gentlemen that try to make repeated eye contact, trust me. On a slow day or during particularly bad weather, you could attempt to strike up a conversation. Weather is always a good topic.

Since you already know she is on your commute often, you don’t have to ask for her number the first time you drum up a conversation. Just a simple weather observation and funny aside could be all you need to lay the groundwork. A first date could always be a cup of coffee or beer as you exit the train station instead of a full-blown evening out.

Commuters that are in their own musical world are harder to strike up a conversation with, but that doesn’t mean you can’t hold a door coming out of a station or smile all the same.

If you feel like the clock is ticking, you could always dig up some courage and just casually say, “I see you on this train a lot, do you work in Midtown/Downtown/wherever the train lets you off?” Don’t ask where she lives because that’s creepy. If she takes the bait, you can then say something about where you work, so it’s a conversation and not just a stalker intro. Again, you don’t have to invite her out on the spot, but maybe just lay the groundwork to ask her out after you chat her up a few more times.

Lastly, check for wedding bands. No use wasting your time on a lady that is already off the market.
P.S. – If your commute involves a bar car on a commuter line, for goodness sake, offer the lady a drink sometime on a Friday evening.

Should Wedding Registries Have Less Expensive Items?


Q. My friend is going to a bridal shower and just about everything on the registry is at least $150. She feels priced out and weird about just giving one small mug that’s still like $60. Should the bride have put on more reasonably priced items?  Audrey, NY, NY 

TN-OK: Ah, the bridal shower. When well executed, they can be a fun few hours to see some of the gifts the couple will start their marriage with. When showers (of any kind) are not fun, they are truly soul-sucking afternoons.

So let’s talk registry. The couple certainly doesn’t need to register for anything they don’t want. Perhaps they already have the most perfect wooden spoon on the planet and could not imagine a second one to take up space in the drawer.

I always think it’s polite to think of gifts at different price points, especially if there will be a shower. But every couple is different, and registering should reflect your lifestyle and taste, not just your guests’ wallets. I’ve seen people go the other way and ask for ridiculous items (a pack of kitchen sponges), so it goes both ways.

If your friend feels weird about getting a small gift off the registry, and she shouldn’t, then she’s welcome to think beyond the registry. It is imperative that you show up to showers with a gift to be opened (even if it’s a card with a picture of the large, unwieldy gift you sent directly to the home). Showering the honoree with gifts is the whole point of the event; the honoree should also open them all during the party.

But I digress. Since it’s leading up to the wedding, a tasteful, but fun gift is also a nice idea. A few bottles of wine and a rapid wine chiller sleeve? Some at-home spa items to de-stress as the wedding gets closer? A basket of the bride and groom’s favorite indulgent snacks?

I’m all for going off of the registry, but your friend should also be sure she’s not buying something the couple doesn’t already have, or definitely doesn’t want. Also, if they live in an apartment, it’s thoughtful to not buy another item that might just take up valuable space. There should always be a gift receipt. Gift givers should always ask if there’s a chance the couple will get home, look at the gift and say “what the hell are we going to do with this?!” Another option is to give the entire wedding gift as the bridal shower gift (in this case, it should be a thing, and not a check).

And of course, if some aspect of the bridal shower turns you off—whether the inconvenient location or time, or unreasonably requests on the invite—just send your polite regrets to the host well before the RSVP date. You can always wish the couple well, and shower them with a gift, at the wedding reception.

What Is the Perfect Groomsman Gift?

groomsman-giftQ: What is proper etiquette for a “groomsmen gift” if I have 10 groomsmen? I’m asking them to buy a suit, go on a destination bachelor party and wedding, so I feel like my gift should be bigger than usual. – Help With Gifting, NY

TN-OK: Congratulations on you impending nuptials! Sounds like you have quite a team backing you up. Hopefully your best man can double as a wrangler on the big day.

It’s great that you want to get it right when it comes to the groomsmen gifts, especially if they’re going above and beyond to help you celebrate in style.

Too many people mail it in when it comes to this. It’s an honor to be in someone’s wedding party, but let’s be honest, it can also be frustrating at times. The work deserves proper tokens of gratitude.

Traditionally, the groom gives something like a silver keychain or a watch. Engraved barware or glasses are also popular these days. I’m a traditionalist, so I think it’s nice to give gifts that are useful keepsakes. But there is a problem: If these guys are seasoned groomsmen, they might have more than one pocket watch in a drawer. My husband has a pile of engraved flasks from years of groomsman duty.

Another option is to give experiences. Maybe sports tickets in their respective cities? Gift certificates to their favorite steak house or raw bar? A bottle of preferred alcohol or wine from the year they were born?

It seems as though most groomsmen gifts hover around $75 to $100, although that figure slides up or down depending on number of guys and just how much work went into being part of the wedding party. Ditto for bridesmaid gifts.

Many brides and grooms have some, or all, of the gift be an item to wear on the wedding day, such as jewelry for the women and ties for the men. In your case, where it sounds like all of the guys are really going the distance for you, I would recommend not having a mandatory piece of clothing be the only gift.

That being said, the gift depends on your personality and theirs. Don’t feel like you need to conform to engraved cufflinks if you think that’s lame, or if no one in your wedding party would be caught dead in French-cuffed shirts.

Gifts also don’t have to necessarily be uniform. High-end sushi gift certificate for one guy could then be awesome cufflinks (pieces of seats from Shea Stadium or the old Yankee Stadium, for example) for another. Either way, you want it to be something that they’ll use (or relish the memory of) for years to come.

The good news is most bridesmaid and groomsman gifts tend to be kind of generic, so anything you can do to think outside the box a little will be appreciated. And don’t forget a little something extra for the best man.

Is It OK to Charge Guests for a Party?

retirement-partyQ: After 20+ years of working at the same company, a family member is retiring. Some colleagues are hosting a retirement dinner, but are charging people $50 to attend. The event is being held at nice hotel, so the cost is obviously to cover the expense of the venue. Now, I can’t say that I’ve attended a lot of retirement parties, but strikes me as odd to charge people to attend a retirement party. Is this customary? – MJ, New York, New York

TN-OK: Although I don’t know anyone who has been at the same job for more than 20 years, this question has broad appeal.

The short answer is, no, it is not customary.

I can just hear the haters arguing in my head. “I’m on a tight have budget! Can’t I do nice things but share the cost?” Listen, I get it. Most of us aren’t independently wealthy. But that doesn’t mean you can ask people to pitch in cash because you feel like throwing a party, even if it’s for someone else and your heart is in the right place.

It is tacky to ask your guests to pay money. Period. That is true if you’re inviting people to your home for a party, throwing a shower or having a wedding.

A retirement party is like a shower, sort of. If you host it, you pick up the cost, even if the only person you know (or like) is the guest of honor.

The idea is hard for some people to swallow, because there is a point in time where asking people to pay ($5 for a keg cup, for instance) is totally acceptable. But somewhere after college, it’s just not cool. And even more so at retirement.

It seems as though some people get confused when restaurants are involved. It is customary that when you go out for someone’s birthday, for instance, everyone but the birthday boy or girl pays. But a retirement party is different. People might want to stop by and toast your relative, but not stay for a whole dinner. Birthday dinners, by comparison, are usually intimate affairs.

In this case, I guess it’s good that at least cost is clear up front. But for large parties where disparate groups are coming together, it’s always best to find something that doesn’t require guests to pony up cash to attend.

You have two options:

You can always politely decline and find another occasion to celebrate with this relative, who will probably have a little more free time on his hands. For the same price you can give him a bottle of Champagne to enjoy while watching The Price Is Right.

Or you show up with $50 and a smile (pay in singles, if you’re feeling snarky). Bring the Champagne for your relative anyway, and show those colleagues what good taste looks like.

When Destination Bachelor(ette) Parties Are Too Much

ChrisGoldNY on Flickr

ChrisGoldNY on Flickr

Q: Recently, my husband was given the honor of becoming his long-time friend’s Best Man. The Maid of Honor (MOH) said the bride and groom want a destination bachelor/bachelorette party, which will cost each person in the bridal party $1,000, and probably more.

This is way beyond our budget for such an event, and he has contacted other groomsmen and has gotten the same feedback. He has suggested other events to the MOH, or that just the bridesmaids do a trip.

He is now being pressured to not only spend the money, but also to get the groomsmen who can afford it to help subsidize the other groomsmen who also cannot afford this. I feel that this is not OK at all, is it? — S, Long Island, NY

TN-OK: Around the time that Mojitos got popular, destination bachelor and bachelorette parties somehow became the norm, rather than the exception. I’m not sure how either trend gripped the nation, but the latter can be pretty annoying if not executed with grace.

I can just hear the “What Up With That?” theme song in my head whenever this subject arises.

You are correct that asking people to spend beyond their means because someone is getting married is certainly not OK. Brides and grooms should be upfront about any expectations that are beyond the norm (buying a tux, rather than renting one, for instance) when asking people to be in the wedding party. Mandatory vacationing falls into the exceptional category.

However, I wonder who’s calling the shots here, the MOH or the couple? I’ve encountered as many totally controlling, insane MOHs as I have brides. There’s no reason she (or the bride) should be calling the shots for the guys. Who is this party for anyway?

Of course your husband wants to be the best Best Man he can be. These parties are rarely total surprises, so your husband should go straight to the source. He should call the groom and explain that for him, and the majority (I’m assuming) of the groomsmen, it’s simply too much money.

You already mentioned he has some other ideas up his sleeve, which is great, he should. But since it is about a weekend (wait, didn’t this used to be just one night?) for the groom, is there a way to take the spirit of a destination party and transplant it somewhere closer to home. A weekend rental by a nearby beach or lake? 

Now, if it is only your husband and one other guy who truly can’t afford it, and everyone else is gun-ho, he should still call the groom (or better yet, do this over a beer) and explain the situation. No good friend would want to put his buddy in financial straits over a weekend of debauchery.

Some grooms or other guys choose to pick up some of the tab for friends without the means because they really want them there. But really, destination bachelor parties are expensive, and should always be optional, including for the wedding party members.

It would seem odd that the groom would have his heart set on a bachelor party that half his wedding party can’t attend. And even when people can afford these weekends, there is often plenty of grumbling behind the bride or groom’s back about the cost. The groom would probably be happy drinking beer and eating burgers in a basement if it meant his bros were all there.

I’m starting to think that the destination weekends fall under the category of “payback is a bitch,” since so many people have had to shell out for their friends they feel they’re entitled when it’s their turn. That is not the right attitude.

I have attended and planned destination bachelorette parties – but I’ve also said no to plenty of them. No one has ever said anything about my decline, even when I was in the wedding party. It’s simply rude to not give people an option to decline, which is what the MOH is doing.

Now, I know some people who’ve done both a destination party for those who choose to go, and something local for more friends who can’t, or don’t want to, go on the other trip – for whatever reason. I feel like two bachelor(ette) parties is excessive, but if it means everyone can feel like a part of the festivities, I guess it’s not such a bad thing.

Good luck to your husband! Sounds like he has his work cut out for him.

When Can I Send a Save the Date?

save_the_dateQ. My fiancé and I have been engaged for a few months and just set the date for May 2014. I am so excited I would like to yell it from the rooftops. Is there an appropriate way to tell friends and family without sending out a faux, and very early, save the date? And it is ridiculous to post that info on Facebook? – Claire, NY, NY

TN-OK: Congratulations! Enjoy the bliss of your impending nuptials before the minutia of wedding planning makes you want to break some kneecaps.

You’re right, more than a full year out is a little early for a save-the-date mailing, although I’ve certainly gotten a few that early. You have two options; neither of which involve Facebook.

Some FB friends might be thrilled to learn the date, only to wonder why they’re not invited later on. Other people you wished had seen the post might miss it in their newsfeed of 672 friends.

As you start your wedding planning it’s important to remember that nobody cares as much about this as you do. That’s not to say it’s not important and fantastic. Friends and family are (hopefully) thrilled that you two are getting married, but whether they get the date now or in three months is mostly immaterial.

You could verbally let friends and family know the date as you see them or as you email them about other matters. When you do it in person, you may get enthusiastic hugs and/or a celebratory glass of wine – so don’t underestimate a personalized approach. Facebook will never hug you.

An email to any potential international guests as soon as the date is set, however, is probably a good idea so that they can consider saving for an expensive journey. You could then send an early save the date to everyone else (like 10 months, instead of the classic six).

The other option, which I like less, is to email everyone and then follow it up with the save the date about six months out. The problem here is that you’re essentially telling people to save the date twice. Besides your very close friends, no one is looking for a play-by-play.

An early email may make people wonder whether that is the save the date. Lastly, you’re going to need to email quite a few people for their mailing addresses anyway. In that email you could subtly drop that you’re collecting addresses and the wedding will be next May.

Also, when the save the date goes out, the wedding website should be at least partially functional. You don’t need a registry or photostream yet, but you should have some basic information about day, time and location.

It’s less important (and really, completely useless) to have biographies of everyone in your wedding party up there first. People want to know where they’re going to sleep, not the nickname you gave your college buddy after a legendary night out.

But back to your big announcement. Start slowly by spreading the word, and then design the perfect save the date. Then take a deep breath, cause it’s going to be a long year of planning, but it will all be worth it.

And while Facebook is not necessarily the right place to make major wedding announcements and hope the right people see them, it is a great place to share the small joys (or frustrations) of this once-in-a-lifetime process.

Picking and Choosing Party Guests

google-plus-oneQ: I’m having a party and don’t want my single friend to extend the invite to his obnoxious friend that he sometimes asks to bring along as a plus one.

TN-OK: Ah, the friend of a friend that no else likes. You’re lucky if you only have one of those in your life. I can count at least a few.

Well, the good news for you is it’s not a spouse or significant other, so this is less messy. In that case, you would just have to suck it up if other couples are invited and let this dude mix and mingle with abandon.

Your friend chooses to be friends with this person for some reason, even if the reason is murky at best, so tread lightly.

If it’s a small event, like a dinner party, simply tell your friend you’re having a small gathering. He should know that if you bother to point out it’s small, he shouldn’t bother asking about tagalongs.

On the other hand, if it is a large barbeque or cocktail party, think about letting your friend bring ‘obnoxious friend’ if he asks to. You will certainly be busy enough to avoid him, and your friend will be grateful to not be solo.

Who knows? Maybe this guy will do something so obnoxious it will make your friend never want to bring him by again.