Dating Advice for 23-Year-Old Brian the Intern: Respect Your Capris, However Unfortunate They May Be

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His name is Brian. He lives in New York City and works as an intern at BBH. He's been tasked with making something famous -– anything. As it happens, Brian hasn't had much romance since moving to the Big Apple, so he decided to take the Jakob and Julia approach and kill both birds with one stone –- with a healthy dose of The Bachelor-style edge. Essentially, he's made a YouTube video explaining he is going to go on 30 dates in 30 days and made a site where women can drop their info for him to select from and schedule.

The morning that the story broke on Mashable, I got an e-mail from my editor here asking if I could impart any dating advice to the 23-year-old. This e-mail happened to tumble into my inbox on the same day that I was engaged in another e-mail thread with a girlfriend who was having some issues with her boyfriend and who'd sought me out because, well, I write about this stuff –- I must know something about relationships.

I do know something about relationships. I know that I've had a few of varying degrees of commitment and intensity. I know that they hurt when they end, even when you know they should. I know that often it is better to leave than it is to settle. I know you should be clear about what you expect, but be aware people change and these expectations may change with them over time.

But do I know anything about dating?

I thought I didn't. I even made a joke to a friend when we spoke on the phone that getting dating advice from me was much like asking the Dalai Lama for fashion advice. But that very evening, something remarkable occurred: I received a text message from a man I'd just met -- at 11:33PM.

All right, perhaps that's not entirely remarkable given the times. What made it remarkable was my reaction: I was horrified.

Mind you, being mistress of my own schedule and generally being more inspired during the night means I keep some strange hours, so I do certainly send messages late. But I have never done so with someone I have just met unless the conversation via text message is ongoing or I know the person more intimately, say via the web.

It got me thinking about common courtesy. And the more I thought about courtesy, the more I realized that half of the unfortunate circumstances we encounter in dating could be avoided if we as a culture still had some sense of it.


Brian has completely bypassed what may be one of the most challenging parts of dating by making this into a campaign. The benefit here is that the exposure he gets will reach more women and that may increase his chances of finding one he likes. The downside, of course, is that it feels less genuine, which may cause women to hesitate –- not to mention that the probability of gaining a level of notoriety may attract the wrong sort of woman altogether. I will come back to this in a minute because I do think some things beyond the Internet tie in here, such as the notion of dating for status or gain.

But first, let's say you don't have a YouTube video on Mashable or a website where you can take in women's information and screen them for the purpose of arranging a dating marathon.

Traditionally, we counted on friends, relatives and organizations to meet other people. Nowadays, we have the Internet and social media which can enable us to reach a greater number of people. I like social media outlets (note: not dating sites), because they enable us to connect with a person and get to know them in a less contrived way. We can see spontaneous status updates, candid photos and things they're working on, little things that put together give a much more complete image of a person than a dating profile ever could.

Interacting with someone on a social network can help them become familiar with you even if you have only met once or twice, and give occasion for a date. For example, I discuss operas and symphonies on Twitter sporadically, and have on occasion mentioned my favorite. After some interaction with a man, a direct message from him asking me whether I might accompany him is nearly impossible to resist. Why? Because it shows he has been paying attention. Attention is important -– we'll get back to this also.

Let's go back to asking for a moment because here is where a lot of people fail. Who hasn't experienced the non-date date, that occasion so ambiguous, one isn't quite sure whether it's a date or not? In Los Angeles, the city where everyone is looking for a lucky break, it is the fashion to have “business dates” where someone uses the excuse (however genuine) of helping someone else further their career with an obvious ulterior motive.

Avoid this –- it is both tacky and it exposes the person doing the asking to individuals who may take advantage of them. Rejection is, understandably, an unpleasant thing. But I am of the mind that everyone deserves to be with someone who appreciates them for who they are, without need for any extraneous benefits such as career advancement, social status, a title, and so on.

If you like somebody, ask them clearly. You're setting down the groundwork for a potential relationship, remember, so everything you do should be an honest reflection of the sort of relationship you have in mind. Which brings up another point: asking someone to a date to the opera when you actually hate opera is tantamount to lying. Don't do it! Being accommodating does not mean you should change yourself. Be who you are and stick it out for a person who appreciates that -– you'll be surprised how many people who don't share your interests may still be interested in spending time with you.

This is the part where I tell Brian not to change those capris for anything other than himself. Those capris, however unfortunate, represent a choice he has made. A woman who finds them ridiculous represents the choices she has made. They may still work it out, but there should be no changing to please someone. Compromise should be fair, it should not be an abdication of self.

Back to asking. Be specific and give the other person enough information to make a decision –- and enough time to prepare. A lot of people consider impromptu dates to be tantamount to the assumption that they have no life and may decline on principle!

To illustrate the proper way to ask, let's go with the opera example: “I have tickets to La Traviata next week Friday, and I would be flattered if you would join me.”

Being specific has a perk: if the other person declines, you can always pretend that it's because they're otherwise engaged. Please note that another person does not need to tell you why they're declining, and it is not appropriate to ask or pressure them. Jackie O was notorious for gently declining unsuitable men by saying simply, “I'm flattered, unfortunately, it will not be possible.”

If the person you're asking does express a sincere interest and suggests you may do it some other time, you may take this as indication to ask again at a later date. Here, it is appropriate to ask when it may be a more convenient time. If they are ambiguous, put the ball in their court by asking them to reach out when they are more available.

If you hear nothing and ask again to be declined again, I would move on. They may be sincere in that they want to meet with you, but if they can't make the time for an evening out with you, do you really wish to date them? The alternative also is that they do not want to date but do not wish to embarrass or hurt you by saying so outright.

This is not a reflection of how desirable you are, it is merely the opinion of one individual. Remember this. Under no circumstances are you to berate someone you have asked out for not finding you desirable or not giving you a chance, or doing anything that may embarrass or inconvenience them. That is outrageous and if I had it my way, offenders would be waterboarded.

But I digress.


As I mentioned a moment ago, some people become quite combative when one declines an invitation. It is unfortunate, but it is better to be clear than to be ambiguous and expose yourself to more uncomfortable situations because the other person doesn't get the message. I mentioned that Jackie O was very gentle with her suitors. This is fine, but I prefer a little more clarity: “I am flattered that you would think of me, but I am not interested.” Avoid things like “right now” or “at this time.” Those responses may inspire your suitor to try again.

If you are declining because you genuinely are not available, you may offer an alternative to the person asking, such as “thank you, but unfortunately I have a previous engagement that night. How about next week Thursday?” Note it into your planner as soon as possible so you don't have to back out.

In the event of a cancellation, it is important to give the other person as much time as possible to make the arrangements for the cancellation. It's not always possible because life is a funny thing, but try to stick to the 24-hour advance notice rules as much as possible and be sincere in your apology.

Standing someone up is a grave offense. Respect other people's time.


If you asked someone to do something, the arrangements for the outing fall on you –- unless otherwise discussed. You must make the reservation, procure the tickets, and, yes, pay for whatever incidentals.

If you didn't specify what you were doing, only that you should do something, it falls on the person asking to make the arrangements as to inconvenience the other person as little as possible. In New York, where Brian lives, things are a lot closer than in Los Angeles, where I reside, but even so, if no specific plans have been made, it is always appropriate to ask in what neighborhood or borough a person resides so that, in the event that they opt to meet you somewhere, they do not have to travel too far.

There is nothing worse than suggesting someone meet you if you're the one asking. Always ask whether you can arrange for their travel regardless of where they are. They may decline, but the appropriate thing is to ask.

This is doubly important of dates that occur out of the city. If you ask someone out to a weekend getaway in, say, Park City, the assumption is that travel is included in the offer unless otherwise indicated, not the other way around. Let me tell you, there is nothing more gauche than a man who wants to spend his time in Majorca with you -– could you meet him there?

I don't think so.


Obviously not everyone can fly someone out of the country. In fact, given the economic climate, paying for a nice dinner with any frequency may put a serious strain on our finances. While I would not suggest discussing one's economic situation in great detail, I do believe in a level of disclosure. If you asked someone on a first date and had a great time and wish to do it again and the other person agrees, it is fine to let them know that as much as you'd love to take them somewhere fabulous again, that you need to watch your spending and how about a picnic at a botanical garden?

If not much for the outdoors, the other person may suggest a more economical restaurant alternative that they love (every city has these hidden jewels), or even offer to pay the next date. It is perfectly acceptable for a woman to split the bill or pick up the tab entirely -– but be sure that you disclose something to this effect before the date, not during and certainly not after the bill arrives.

The matter of spending ties in to the little lecture I gave on honesty earlier. If you do not have the means, do not pretend you do. More than anything, it is a disservice to yourself. Top chefs and ambiance are a wonderful combination, but it should be more about your company than the newest restaurant in town.


We skipped a part, didn't we? We're already at the bill and I've hardly said anything about preparing and going on the date itself, which is, after all, the main event.

For starters, dress for the occasion. A date should not be an event that requires a tremendous amount of preparation, but it does require some and certainly attention to details matters. If you're going to the opera, as we chose in our example earlier, consider the night and your seating. Dressing for the balcony on a random weeknight is far more casual than, say, the founder's circle on opening night.

That one may seem a little trickier, but consider something like dinner at a restaurant on the beach that may include a stroll on the boardwalk. If you suspect you are going to be doing any walking, you must keep in mind to don appropriate footwear.

If you're being taken somewhere and you have no idea how to dress, don't hesitate to ask the person who invited you.

Make no mistake, the little black dress (and the male equivalent, business casual), are not always the best solution for the “when in doubt” question.


It is appropriate to confirm on the day of the date. If the date is occurring early, it is fine to confirm the previous evening. Be on time.

While I do expect men to open my door, I have also felt a little ridiculous sitting in the passenger seat of a car while he figured out what to do, so do not be rigid in this regard. A good way to avoid the situation is for a man to ask, “may I get the door for you?” before stepping out of the car or reaching a building entrance. A woman's response will indicate her expectations. This is also the case for pulling chairs. That entire convention largely depends on the preference of the woman in whose company you find yourself.

If it is cool and you are outside, ask whether your date is comfortable and offer your jacket. If at an establishment, ask about a heat lamp. If it is hot and sunny and changing tables is not an option, always offer your date the shade.

When walking on a sidewalk, the man walks on the side closest to the street. If there is a crowd, the man goes before the woman to clear the way for her. It is appropriate to offer an arm. Consider this especially if your date find herself in heels. While doing so, do not remark – under any circumstances – that she seems to be having trouble walking on her shoes. She may be having trouble, but there is no greater indignity than the suggestion that a woman cannot handle her Louboutins. You may instead suggest that you sit for a while or that you procure a cab to travel to the location you're trying to reach.

If you are meeting at a restaurant and the other party has not yet arrived, wait for them to arrive to be seated. If you tip anyone in advance to ensure they're attentive, do so with the utmost discretion and try to avoid your date seeing the exchange, as it often has the opposite effect of being impressive.

Please note that while geomapping services are in vogue a lot of people do not like their location to be known by the general public. Always ask whether it's OK to check in to an establishment on one of these networks before you do so. I have known couples who were joined by friends while out on an intimate dinner date because someone saw they had checked in on Foursquare and assumed they wanted company. The safest rule for using these services, if you should decide to do so, is to check-in after you have left an establishment, not before or during. Whatever the case – always ask.

This same courtesy extends to other social networks, even if you do not specify the location. Does the other person want it to be known they're out? There are hundreds of legitimate reasons why they would prefer to keep a date private. It may also reflect badly on you if you are with a microcelebrity or –- in the case of Los Angeles –- a celebrity-celebrity, and you decide to name drop. You don't want your date to think you're only there to show your Twitter followers or Facebook friends how cool you are.

I don't think I need to say that updating one's status or texting or even receiving a phone call during a date can be construed as a gross infraction, do I? Social media updates are more common, but keep in mind someone has made time in their life for you and, having accepted, you should be spending that time in their company actually being present.

After you are seated and have heard the specials, take some time to discuss what your date wants. It is acceptable for the man to order for both parties. Remember that the best signal that you are ready to order that you could ever give is a closed menu.

While it is conducive to better service to ask the name of those serving you and engaging them a bit, it is not appropriate to carry out a discussion for more than a minute or two, as it can make a date feel like a third wheel. If the server or bartender are of your preferred gender, the conversation, however casual, could be construed as flirting, which is then not only impolite, but outright humiliating for your date. Have some consideration.

It is not beyond the pale to order fewer courses than your date these days, but do let the server know to bring the items together so that no one at the table is left without something with which to occupy himself or herself. It is not necessary to wait until the other person begins eating to commence, but one should wait until the other person is served. If you are served but the other person isn't due to some delay, wait until they are. If the other person encourages you to begin, you may oblige – but slowly and in a considerate fashion. You may offer them a bite of your meal after a few paced bites.

Whatever mishaps, try not to call too much attention to the issue. This is especially the case if you did not choose the venue yourself, as being critical can embarrass the person who chose the establishment. If, on the other hand, the person who chose the place is the one who is being critical, you may reassure him or her by letting them know that you don't care because the company is enough.

Once the food arrives, do not drown your meal in condiments before you taste it. It is a gross disrespect to the chef and the establishment. Mind your posture and your manners. Drink responsibly – especially if you're driving.

If while ordering your date expressed a preference that you find unusual – say she likes her meat “blue” – do not express distaste however unpleasant you find it. Do not lecture her on how unsanitary it is to eat meat nearly raw. This is also the case with smokers. Imposing your preferences is rude. Being curious, on the other hand, isn't. You may ask when she started eating meat that way. Conversely, you may ask her how she arrived at the decision to become a vegetarian. Keep in mind that asking why someone doesn't drink may be a little more delicate.

Whatever the case, do not impose, do not pressure and do not joke about choices, even if your ethical vegan date is wearing leather. Enjoy who they are –- it's why you're there, isn't it?

When the meal is over, place the utensils on the plate in accordance with whatever style of dining you find suitable to the country in which you find yourself (American style places them diagonally, knife to the right of the fork, blade in, and the fork with the tines facing upward). If your date seems as though he or she doesn't quite know which style to adopt, casually show them by doing it yourself without mentioning it. The waiter will see this as indication that you are finished and clear the table. Do not push flatware away to “help make room for dessert.”

When finished, do not refold the napkin! Place it on the left of your plate.


You're dropping off your date. Unless told otherwise, it is customary to walk your date to the door. Do not ask if you can come up. You're at another person's home and they will issue the invitation if they feel it is appropriate. It's fine to suggest a second meeting at this point. You don't have to be specific now, but do let the other person know a time frame to expect doing this again.

If you do this but do not mean it, do phone them within said time frame to let them know that it is no longer possible to see them again. It is discourteous to leave someone hanging.

And yes, it's fine to initiate a good night kiss at the end of a date if you haven't done so already, but move slowly so the other party may stop you if he or she doesn't feel it is appropriate. Paying attention to their body language throughout the date can help ascertain whether this is a good idea.

If you asked them out on the date, it is good form to send them a text message thanking them for spending time with you. If it's late, you can do it the following day.


Now we go back to the thing that started it all –- that text message that arrived at 11:33PM. It's not quite a “booty call” text, but it doesn't sit quite right either. Here's the thing about texting: it's not viewed as invasive as a telephone because you are not expected to become engaged at just that moment. Nevertheless, as mobile devices become more common, we usually have our cell phones on us and unless they're set to silent, a text message is an intrusion into another person's life and this must be considered.

For this reason, unless otherwise stated, keep the hours text messages are sent appropriate. I personally find messages after 9PM from people with whom I am not yet well-acquainted to be impolite unless there is a discussion underway via text or we're trying to organize something later that night or early the next morning. If I am just starting to see someone, I expect him to be more aware of the demands of my schedule and spare myself any confusion regarding “booty calls” by not being subjected to texts after 9PM.

Once we become more involved, this changes, but during those critical first few dates, I take these as indication of how much a man is going to consider and respect my schedule and it could bode very badly for him.

It should be noted also that one message is sufficient. A person needs only one message. If they do not respond, it means they are occupied or do not wish to respond. It is impolite to continue messaging, or to try other media, such as social networks or e-mail –- or worse, all of these.

There is a very, very small probability that the message was not received. Give it a day or two before trying again. If you are thinking of opting for another network to be sure this message is received, it may be time to place a direct call. If you still receive no response, let silence speak for the other person and back off.


Of course, as I mentioned previously, these aren't do-or-die. But sometimes I wonder whether things wouldn't go on a great deal more smoothly if there was some kind of code and everyone was aware of it.

Good luck, Brian. When it comes to dating, the Big Apple is no piece of pie.

AV Flox is the editor of Sex and the 405 -- what your newspaper would look like if it had a sex section.


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