Advice

Valentine's Day can be a stressful holiday for single people, but it can be an even more frustrating experience for those who are coupled up. For those in a long-term relationship, where this is your 2nd or 3rd or 15th Valentine's Day, it's easier. You know what your partner expects and you communicate well with each other about your needs.

But if it's your first Valentine's Day together, what do you do?

If you're lucky, you and your partner can have a discussion about the holiday and decide what to do together. Will you buy presents? Will you plan a romantic dinner out that night? Will you cook dinner together at home? Will you celebrate Valentine's Day out a day later to avoid the crowds? This can all be decided through frank and honest communication with your partner.

However, I'm not here to talk about all that... I want to tell you the story about a guy who sealed the coffin on a relationship with me on Valentine's Day.

This guy, we'll call him Mike, was a sweet guy. We had started dating in late January and had a couple nice dates for dinners and movies. He'd taken me to his job in a high-tech industry and given me a tour of their facilities. By the time Valentine's came around, we had been on about four dates.

We'd kissed a lot, but that's about as far as it had gone. It was very much still in the "we're dating" stage, not the "we're boyfriend/girlfriend" stage. And to be honest, I was having a hard time seeing us making the switch. There were things about him that just weren't clicking for me and (more honesty!) he was an AWFUL kisser. It was like his jawbone was crushing my face. I tried to nicely guide him in the direction of the type of kisses I like, but he wasn't very teachable.

But the nail in the coffin was the Valentine's Day card he gave me. Now, there are thousands of Valentine's Day cards to choose from in your local store. There are cards for spouses, cards for boyfriends/girlfriends, cards for other loved ones, serious cards, sappy cards, funny cards, non-committal cards. TONS!

What card did he choose for me? One that read like a love poem about our deep intimacy and affection and wished for us to grow old together. Seriously. It's something I'd expect after being married for five years, not after going on five dates.

The moral of the story: When in doubt, go for a funny Valentine's card. You can SHOW more love if you want, but you can't un-show an overly sappy card in a relationship that's not at that point yet.

Now you know, and knowing's half the battle!

I've heard this one more than once: “I didn't want to say I was meeting someone from the Internet, so I said I was going on a blind date” or “We told people met on a blind date.” Some feel that online dating has enough of a stigma that meeting on a blind date is preferable. And in some circles, they might well be right. My question is: why?

Why is a blind date so much better than meeting someone through an online dating site? Let's think about what a blind date actually is: someone theoretically close to you (though not always) thinks you would hit it off with some other person, so you go on a date to find out. That's it. The person you might not trust in choosing a sweater for you gives their two cents on your love life, and you listen.

With online dating, you're choosing the potential date yourself. You have at least some hints about their personality and appearance, and you have your gut instinct. Hopefully, you've been chatting as well, and you think there's intellectual chemistry. It would appear to be a much more informed, responsible decision – so why cover it up?

Maybe the appeal of the blind date story – and blind dates in general – is that in a blind date, someone is essentially vouching for the stranger you're about to meet. This may be true in theory, but often the person facilitating the blind date is only acquaintances with one or more of the people involved.

To me, claiming you're going on a blind date instead of an online meeting says more about you – your self-esteem, whether you want to claim responsibility for your decisions or be passive – than what the other person will think. Be bold and stand behind your decisions! If everyone does this, soon we won't be worrying about a stigma at all.

Valentine's Day is coming up quickly, and a reference to Valentine's Day might appear to be the quickest and most obvious way to update your online profiles. However, as you sit down to compose your update, beware! Valentine's Day is a holiday loaded with meaning for many, and often the meaning is quite different depending on who you're talking to.

For example, a simple “Looking for a Valentine” is probably heartfelt and topical. Get any more specific, though, as in “Looking for a date this Valentine's Day” and the reader begins to wonder: are you desperate? Are you only worried about a date for this arbitrary day? And if you're letting an arbitrary day get under your skin that much, are you superficial in general?

Then it's possible to go too far in the opposite direction. You might want to give the impression that you're confident and unaffected by silly holidays, so you might toss out something like, “Looking forward to Valentine's Day... when else can I sit alone on my couch with a box of chocolates and a bottle of wine?” Some might find something like this funny, but it walks dangerously close to coming off bitter. Humor is always tricky on the Internet, and with a profile it's a extra hard, as there's no additional context like previous emails to get the tone of the writer.

So, what's the safe middle ground? Go for silly, happy and cheesy. Maybe mention that you're glad to have an excuse to wear that tie with purple and red hearts this month, or that you're going to bombard your office with superhero Valentine's cards. You could wonder aloud why supermarkets sell Valentine's Day-themed stuffed animals that are often monkeys or elephants. Stick to the fun of the holiday, without assigning meaning to it, and you'll avoid being misunderstood.

Still, the easiest answer is: Don't tread into that Valentine's Day land mine at all. Update with something more innocuous and less loaded, like you're already searching the ground for the first hint of spring or how you're so excited at a thaw that you're running around in shorts. Lame as it may sound, the weather is current, safe, and easy to apply your own flavor, whether it be romantic or funny. Leave Valentine's Day to the kids with the stuffed animals.

In the past two weeks, I have had two dates with men who consider themselves a "starving artist." One was a sculptor, the other a singer. Neither appeared to be making an actual living from their primary pursuits. The sculptor revealed that he had grown up on Park Avenue and had a quaint country house in Maine (Hmm... where is the "starving" part of this artist?). The singer, over wine one night, told me that he paid his bills by waiting tables. If things couldn't get bad enough, he told me he was a singing waiter.

Both men were approaching 40.

Admittedly, I don't pull down all that much income. I make enough to support myself and get by and pay my bills. But I am not living the high life by any means. But, at 41, I actually earn a substantial living from my job and support myself from it. I don't have to take side jobs to pay my bills. As a fully fledged (well, pretty much) grown up, I know that I shouldn't try to live outside my means. Which is why I was totally shocked when the sculptor explained why he didn't pay the bill was because he was "a starving artist." Now, the tab was not all that much. $50. So I couldn't help but wonder why, if the extra $25 was going to break his bank for the week, he went out in the first place. I mean, if you have so little wiggle room that $25 could set you back, my thought is ... stay home. But that's me. Even more shocking was that he still insisted on walking me home and kissing me several times good night, likely pulling a Hail Mary Pass by trying to land himself in my end zone despite not paying the check.

The situation with singer was different. I willingly offered my share of the tab. Not only did I not sense any attraction for him, but I couldn't imagine letting someone who probably was scraping by pay for my drinks. That's a general rule for me. If I don't think there's any chemistry, at least enough for a second date, I offer up my share. I don't let a man pay my way when I don't believe he'll receive his return on investment.

I know how this makes me sound. It makes me appear shallow. Think what you will. The biggest mark against these men wasn't their lack of extra income. It was the fact that that were both approaching middle age and still insisting on pursuing a career that possibly did not support them. This is fine if they wish to live a life without a serious relationship. But how can you even imagine creating a partnership with someone else when you can't pull your weight financially? Not only that, but consider the emotional strains placed on a relationship where one partner isn't doing their part. Success in any arena is heavily dependent upon the person seeking success devoting a great deal of their time and thought to achieving said goal. That doesn't leave a great deal of room for a partner to be a priority. Something, in that equation, has to give way.

Let's be clear about something. I will ALWAYS support and be the cheerleader for someone pursuing a dream, regardless of how old they are. But that person needs to be able to support themselves first before they risk it all. They also need to demonstrate that they have an understanding of what's at stake if they do not succeed. Finally, they need to live their life as though they are planning to bring someone in to it. That requires that they know and understand that their partner might find their current lifestyle concerning

I think this is more of an issue for women than it is for men. Unless a woman represents some kind of potential financial burden on them, they don't care if she's a struggling actress of writer. It's different for women. Maybe it's because men are "supposed" to be the financially responsible ones. Sure. That's part of it. The other huge part is that being involved with someone who's on unsure financial footing will require an even bigger emotional investment on the woman's part. We'll be expected to not only emotionally support him (and possibly financially support him) but also continuously stroke his ego. Then there's the emotional roller coaster that comes with all of that. It's a lot of work.

Here are my final thoughts .... becoming an adult means giving up on certain pipe dreams and accepting certain realities. Being a part of a loving. mutually beneficial relationship means continuously striving to be the best partner you can be. If, by 35 or 40, you're still choosing a certain path and it's not one that comes with a certain level of stability, then you need to decide how important a relationship really is to you. It's fine if it is not as important as your career. But be honest with yourself. Realize that you may be pulling other people down while you try to build yourself up.

In today's world of telecommuting, non-traditional work and home environments, people tend to feel that their dating options are increasingly limited. If you work from home, don't like the bar or club scenes, don't attend a church and aren't having much luck on the Internet, where can you turn?

My proposal: volunteering. Not solely as a means to find a date – that's a little like the sitcom boy joining the sewing team because it's full of girls. I'm suggesting that those who are having trouble meeting people of any sort – friendship counts too – turn to something they're passionate about, and volunteer a bit of their time.

When most people think of volunteering, they think of building homes or serving at a soup kitchen. Those are certainly worthy causes, but there are countless additional ways to volunteer. For example, a group of musicians might stage an instrument open house for children. Someone who's had their life affected by an illness or disease might want to help out with one of the many marathons. If you're into comics or science fiction, many areas have local conventions that can always use volunteers. And, of course, various holidays and seasons provide additional opportunities to help out.

Volunteering helps in countless ways. First, there's the obvious benefit to whatever cause we're working for, whether it's playing checkers in a nursing home or taking care of rescued animals. Then there are the lesser benefits: we're thinking about someone other than ourselves, so it can often lend some needed perspective to our busy lives. Helping out a cause we feel passionate about makes us feel good, so we're generally at our best. And, finally, working side-by-side with others who have the same passions means we're meeting new people, and we've already got something in common.

So if you're feeling down about the way things are going in your life, volunteering for a cause you care about is a great way to turn it around. It's also a fantastic way to meet people who could become friends – or maybe even something more.

I'll be the first (and certainly not the last) to tell online daters to STEP AWAY FROM THE WINK BUTTON!

All too often, people use the wink function as the lazy way to tell lots of people that they find them attractive. In fact, there are many men out there who don't even read your profile, ladies. They just look at your main photo and decided if you're wink-worthy.

(This is why I tell my female clients not to get worked up if a guy who is totally incompatible winks at them. Just close out the match. Nine times out of ten, he won't email or bother them again.)

But there is a time when you can wink!

Are you ready to learn the magic time?

... are you SURE?

Okay, I'll tell you. The magic time to send a wink is immediately AFTER you send a short and sweet, personalized email.

Here's why:

If you're on a site like Match.com where there are paid and unpaid members, your email is only going to be read by the paid members. Unpaid members cannot read email. They can see that they have email in their box, but cannot even see who it is from. This mystery is what prompts many people to whip out their VISA and pay for a subscription.

If an unpaid member sees they have an email and also a new wink, they may make the connection and say, "Hey, I wonder if the email is from this guy/girl. They look pretty awesome!" Then they may be motivated to pay, read your email, and reply. WIN!

If a paid member sees you've emailed and winked, it's just a way of saying that you're really interested in them. WIN!

Practice safe winking and you'll most likely see a much higher response rate to your messages, and isn't that what we're all shooting for?

To find out more information about the dating site mentioned in this article, read our Match.com review.