The First Hello – Long Term Relationships vs. Casual Dating 

Congratulations. You managed to find someone who piqued your interest on a dating site, and she might want to meet you.

Now what?

The following is my attempt to give you some advice in two entirely different directions depending on what you really want to achieve, since different answers and choices can lead in different directions. The most relevant question here is: What are you hoping for?

Allow me to just be blunt. Some of us are serial daters. We love to meet women, we love to court them and bed them, but then, well, we’re pretty much done with them. Sometimes it’s because we have serious commitment-phobia, and sometimes we just like the thrill of the conquest and not the white picket fence part. Personally, I like to think of myself as spectacularly fun dating material but lacking most of the requirements for long term relationships. I also lack a plush bank account, stability or startlingly handsome good looks. So, I date. You, on the other hand, might have what every woman ostensibly wants (a bottle of Chateau d’Yquem and an AmEx Black Card), and you might be looking to settle down. My point is that whichever direction you desire to go should determine how you move forward.

In simple terms; if you’re looking for a long term partner, my advice would be for you to strive for brutal honesty and complete transparency. You want to scare her off, if possible. While that might seem counter-intuitive, it actually serves your long term interests well. You want a partner, not a waste of time or a weekend adventure, so your focus should be on vetting out all those except the women you really think you could have a good go with. The best way to do this is just to be honest and ask difficult questions. It shows her you are serious, and it shows you who she is, in depth.

On the other hand, if you’re like me and just looking for variety and spice, then you need to approach the entire meet/greet/play from a completely different angle. Do NOT tell her your life’s dreams and aspirations. Don’t ask for hers. That isn’t the point here. Here, the idea is to make her swoon. One of my favorite lines is from the Stephen Sondheim musical Into The Woods: “I was raised to be charming, not sincere,” spoken by Prince Charming when Snow White catches him sleeping around with Sleeping Beauty.

OK, I might take some flack here for being apparently misogynistic in this regard though again, I repeat that being clear on your end goal is important. Having fun is not the same as finding a new mate. It just isn’t. Of course, you shouldn’t be lying to anyone or cheating or being intentionally deceitful. It might improve your chances of getting laid, but it won’t help your karma much. Besides, liars suck: we all know this. So don’t be one. That doesn’t, however, preclude your ability to keep details hidden, to allow yourself to be perceived as slightly opaque or mysterious, or to keep the conversation focused on her. Think of this strategy as airbrushing your best features.

If you’re seeking long term results, you want to make sure she can appreciate who you really are, and you want to show her your warts so that she might come to love them. If you just want to have fun on a Friday night, might I advise that showing your warts is not only unnecessary, but counter productive to a good time. If you show up in a suit, you don’t need her to know it’s your only one.

So, here are two little lists (in no way complete) I came up with to give you some clear ideas on how to approach your next conversation with a potentially interested party, keeping in mind the agendas of casual dating vs. a serious relationship.

Keep these in mind if you are only dating:

– Remain mysterious

While you don’t need to be so secretive as to seem suspicious, there is also no reason in a dating scenario to bother her with your life story. That’s not what we’re here for. Keep the focus on her, but…

– Don’t ask too many questions

Of course, ask questions about her. Just try to keep them light and conversational. Fads, trends, the latest news, etc… we’re not looking to find out if our political or religious views match yet or how many bad relationships we’ve survived or the name of her dog that just died. Save the messy stuff for later talks if you find you’re getting serious.

History is great if you’re working to establish common ground. Talking about the present is great when you are looking to move forward, which is what dating is.

You absolutely want to talk about her as much as possible, though you should be careful not to be entirely irrelevant to the present. I’m not saying that knowing where she went to high school might not be interesting, or learning that her sister lives in the same city you grew up isn’t serendipitous; I’m just saying it isn’t important. Question her instead about her desires, her tastes, her interests, her work perhaps, her schedule and availability (to know when to ask her out again).

– Close for a meeting

This mainly applies to online dating. If you’ve received a message of interest, and you want to date, then your next message should be to ask for one. Offer a few ideas and an alternative time, “Would you like to go feed ducks at the park, or maybe meet for a cup of coffee? I’m free tomorrow, or if that’s too soon, how about Thursday afternoon?” Note: You also want to be certain to include a sincere compliment that shows her you’ve noticed her as well — and a thank you in that response, at the least.

– Plan A, B … maybe C

When you meet your date, be ready to keep her entertained. Have multiple ideas of where to go and what to do in mind, so you can appear casual and confident with a plan. Seriously, most women love a man with a plan, and love a man who can turn on a dime with another one even more.

– Unless they want control, you take it

Not all women want a man with a plan. Sometimes they have their own. It’s always a good idea to check in at the beginning of an engagement to see where she stands. Just ask her, “Listen, I have some ideas about what to do tonight, but I wanted to know if you want me to just take charge, or if I should ask you first?” Deferring to the woman gives her the chance to let you know, and subtly shows off your gentlemanly ways. If she says anything along the lines of “Just surprise me!”, which most will, that’s your invitation to make all the right moves.

– Be open minded / Go with no expectations

When dating, the key word here is; Fun. Having fun means being open to whatever happens, and seeking intentionally to do things that are silly, irreverent and able to bring out the kid in ourselves. We need to approach our dating that way. After all, we’re likely going to know in the first five seconds whether we have a chance of anything progressing beyond the date, regardless of the date itself. So have fun, and be open to someone else that you may be otherwise uninterested in. You never know; perhaps the person holds back so the first impression was aloof, but the moment you cracked the right joke, the ice melted.

– Be clear, courteous, concise

Think about your words before they tumble out of your mouth. If you’re meeting her, give good directions or ask for them. Show her that you are personable, intelligent, competent and capable by speaking confidently, with grace and clarity. If you’re shy, practice with a friend. Learning to speak so others listen is an important skill worth developing.

– Flirt

Finally, this is a skill that others have devoted tremendous amounts of time towards explaining, so if you don’t know how, go learn. Since this is a date, if you think that things might heat up, then you should push for that. You’re not trying to demonstrate yourself as good husband material right now, you’re trying to get laid. A kiss goodnight is not really your target resolution for the evening.


On the other hand, try this approach if you are seeking a long-term relationship:

– Remove mystery, be real

Ask for — and tell — the truth. We’ve all had messy lives. While you might not want to begin your communications broadcasting your less savory traits, you need to be honest about them. Do not avoid difficult questions in the early stages here. Embrace them. You’ll see quickly if the person in front of you is willing to accept you for you. Put the warts up front.

– Talk about upbringing, family, goals, history

Instead of the shallow, trivial conversation, ask instead about things you’ll really want to know about this person you are considering spending a great deal of time with. Don’t be afraid to push a little and see what they are willing to talk about. It doesn’t have to be weighty, but it should be authentic.

– Attempt no closing statements and let her take the initiative if she wants to meet you by making yourself available but not pushing

In this way, you aren’t working to steer her in a direction so much as trying to ascertain her feelings towards you. If she wants more, she’ll ask. Remember, there is no rush when seeking a long term partner. If she doesn’t seem too interested, that’s just fine in this scenario.

– Watch closely for red flags

Red flags might be more easily dismissed on dating, but should be clear warnings in long-term seekers. While her love of a music you find vile might be easy to deal with when you are seeing her once a week, if you come home to it every night, it’s going to be an issue. Just pay attention to whether you feel comfortable and relaxed with her, or if you feel as though you are having to prove yourself.

Be certain of your expectations and desires and only flirt once you have determined you really do want to know more

While we may choose to engage others for short-term pleasure seeking or simply in order to have a nice person to pass a little time with, even in a favored “Friends With Benefits” category so many single men profess to prefer, we shouldn’t lose sight of our long-term goals especially when we find ourselves genuinely attracted to someone. If you believe that this new person may very well be someone you desire to be with long term, then it behooves you to move slowly in your romantic gestures. That way, when you act, it will carry that much more weight and sincerity. A rose is nice, but a gift from the heart is far more valuable. A kiss goodnight here means volumes more than a one-night fling. Save yourself because you’re worth it, and so is she.


Closing thoughts

I make no guarantees whatsoever that my advice is going to turn you into a dating guru. I just know that you attract what you ask for, and if you’re seeking one while believing you’re seeking the other, you’re going to have problems. I also know that dating requires attraction and chemistry in the short run, and you can enjoy many different types of people even if you might not be able to have a healthy long term relationship with them.

Simply put, dating is fun. Relationships are work.

Of course, the person you commit to the long term with should be fun, too. In fact, even more fun than someone in a dating relationship. The difference is that you’ll need to spend the time to find the things that really connect you, not just those casually shared appreciations. These require levels of communication and honesty that take time to develop.

While I do suggest considering the approaches above, there is nothing to say that your casual date won’t turn into a long term commitment, or that while seeking a long term relationship, you’ll have a few short-lived dates (in fact, that’s almost a certainty!) Just knowing how to approach the next pretty woman who makes your heart skip a beat can make all the difference in the world.

Good luck out there!

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