Practical Tips for Early Dates
Navigating the Minefield of Mature Dating Expectations
If you’re a little out of practise with dating, you might find the prospect of planning and attending dates with new people a little daunting. Where should you go? What should you do? Who should pay? What if she has catfished me? What if she stands me up? What if I don’t like her in person? These are all valid questions, and we’ll help you answer them in this article.
First Date Protocols
Since the proliferation of online dating, the first date is now more often than not the first time you will meet in person. This serves as an opportunity for each of you to form an impression of the other and gauge whether it’s worth investing your time in a subsequent date. In other words, it serves as a litmus test or an initial filter, and it’s best to keep this date low-key.
First Date Venues & Activities
If you don’t already know each other in person, keep in mind that your date probably has a bunch of options (as should you), and little incentive to invest a lot of time and energy into this initial meeting. You’re both busy people, so find half an hour to meet somewhere mutually convenient where you can have a conversation. Avoid fancy restaurants and noisy bars or nightclubs. You want a quiet cafe or bar, or a pleasant outdoor space where your date will feel safe to meet with a stranger, and you can enjoy a relaxed conversation. A takeaway coffee or gelato to eat in the plaza, or a couple of juices and some sort of snack to share in the park are all perfectly suitable variations on this theme if you want to get creative.
Keep it On Time
By setting the expectation of the date lasting no more than half an hour, you both have the assurance of being able to leave the date at a specific time without appearing rude. It also makes it easy to deal with someone who disrespects your time by arriving excessively late. The question of “How long should I wait for someone who appears to have stood me up?” becomes easy: enjoy your coffee while you relax for half an hour, and then leave as planned. If they arrive twenty-five minutes late, you still have a whole five minutes to assess their demeanour when they arrive (are they sincerely apologetic or just self-interested?), and decide whether to give them a few extra minutes, schedule a followup date, or simply call it quits with them.
Sometimes you will have an amazing vibe on the first date when you’re both feeling the chemistry and time flies too quickly. If that’s the case, you might consider suggesting an impromptu extension of the date by going to another venue or taking a walk. The change of scene is important, as it accelerates the building of trust and rapport by creating he feeling that you’ve known each other for longer.
If you’re not feeling that vibe, don’t try to force things and stick to your agreed time window.
First Date Financials
The question of “who pays?” is a minefield in its own right. Some women expect a man to at least offer to pay, some feel that if a man pays he is doing so to make her feel an obligation of sexual debt to him, some women find it important to assert their financial independence by paying their own way, and some other women simply date to take advantage of the generosity of men who feel obliged to pay because “that’s what gentlemen do”.
Rather than stumbling straight into this minefield, you can simply skirt around the edge by keeping the budget to a minimum. Most of us are in the fortunate position that the cost of a couple of coffees represents pocket change, so it should not be a big deal however it plays out. Whether you choose to pay the whole bill, offer to pay it, or simply split it right it away is entirely up to you. You should make this decision according to your values and beliefs and never second guess how your date will react to it. If she raises an issue with your decision, explain your position, but also acknowledge hers. Is this a dealbreaker for future dates, or is there a mutually acceptable path forward - perhaps she can pay next time? Keep in mind that your words and actions in this moment could set the pattern for future dates with this person, so don’t insist that “if I invite someone on a date I always expect to pick up the bill” and five dates later get annoyed that you’re the one paying for everything!
Break the Touch Barrier ASAP
You want to “break the touch barrier” sooner rather than later for a couple of reasons:
studies in hospitality suggest that people tend to form a stronger liking for strangers who touch them appropriately than those where there is no touch. (Measured by tips given to wait-staff under controlled studies)
if you put off touching someone you find attractive, the idea of touching them often becomes a “big deal”, to the point where it could become awkward to touch them at all.
How you achieve this is largely down to your personal style, local culture, and the level of rapport you’ve already established. If it’s normal for you to greet female friends with a brief hug, go for this approach. At the very least try for a gentle touch to the outside of the upper arm while talking - e.g. to emphasise how pleased you are to meet her in person. Remember, she is equally likely to feel a bit awkward about what’s expected in terms of greetings and goodbyes, so respectfully take the lead with confidence and she will almost always go along with you.
See the following article for more details on the importance of touch and how to escalate:
Whether it’s a appropriate to escalate touch throughout the first date will depend entirely on the circumstances, but if it’s obvious that this is just a “filter” date for her to determine if you’re who you say you are and confirm she doesn’t get axe murderer vibes from you, you will likely have little opportunity for physical contact between greeting and goodbye.
Conversation is Key
Have you ever been on a date where she fired a string of questions at you that felt like a job interview? Nobody likes that, so don’t be that guy!
On the other hand, have you ever been with somebody who liked the sound of their own voice so much that talked incessantly about themselves, no matter how many times the topic changed? Don’t be that guy either!
Let’s be clear: your objective for this thirty minutes is to make an emotional impression on your date by making her feel good about spending time with you.
More importantly, let’s be clear bout what you are not here to do:
Convey all the logical reasons you’re such a great catch by talking about your career, your achievements, your wealth etc.
Entertain her with party tricks, pre-rehearsed anecdotes, jokes, or your life story
Answer a bunch of boring questions that are irrelevant to whether your values align and the possibility of the spark of attraction exists between you.
It often helps to think in advance about the common ground you share as the starting point of conversation. This might be interests or experiences you share, which might be as simple as your experiences with online dating. This can help you break the ice, but you’ll quickly want to steer the conversation to more enjoyable and engaging topics, such as exploring her interests. She will likely redirect to you throughout the conversation, in which case you should answer appropriately before redirecting the conversation back to her interests. This is the time to “be interested to be interesting”. (See the related article for more in depth advice about conversation techniques).
Second and Subsequent Dates
Once you’ve met in person, each of you needs to decide:
Do I feel sufficient sense of attraction and potential relationship with this person to invest more time in getting to know them?
There are so many factors that inform the answer to this question, and very few of them are in your control:
Maybe you have an amazing rapport in conversation, but in person there was just no chemistry.
Maybe she finds your personality irresistible, but in person you remind her of an ex who left her traumatised.
Maybe after meeting you she feels that you have your life together in a way that she doesn’t, and she feels intimated about pursuing a relationship with you.
Maybe she was amazing to chat with and stunning to look at, but she disrespected your time or was rude to the staff at the cafe.
The lesson here is that “failing fast” by avoiding second dates that are unlikely to lead to a meaningful relationship is ultimately a good outcome, so do not be disheartened if she doesn’t want a followup date, and feel confident in your own decision not to pursue followup dates with women you don’t feel strongly about pursuing.
Second Date Activities
In most instances you’ll still be in the “getting to know you” phase of the relationship by the second date. This means you’ve passed the initial test of “smells OK and doesn’t have axe murder vibes”, but have not reached the level of “I’m already imagining what our children will look like”. That means you will want to continue to keep the emphasis on spending time together getting to know each other without the complication of financial friction or other factors that could be perceived as coercive.
Choose an activity that encourages conversation and where the cost is negligible. Possible suggestions might include:
Cafe brunch or lunch
Picnic (somewhere that affords a modicum of privacy without being completely isolated - e.g. a park or a beach rather than a remote lookout or forest trail)
Food or Wine Tasting
Walk - e.g. an urban walking trail, coastal walk, etc
Visit a weekend market
Visit a gallery or exhibit (assuming you share an interest in that type of art)
Avoid activities that make it difficult to talk. Save the movies, concerts, and other live shows until you reach the point where you simply enjoy being in each other’s company without the need for conversation.
The Importance of Tension
Assuming the first date was just a filter, the second date is likely to be the most important in determining whether or not a strong spark of attraction exists between you. It’s up to you to ensure that by the end of the date she is thinking of you as a lover, not just another male friend.
This means you will need to lean into the tension between you by:
using your body language to convey confidence and desire
using verbal communication skills to flirt and inject a hint of sexual undertone to your conversations
using physical proximity and touch to build intimacy and sexual tension
You can find more detailed “how to” information here:
Remember, the outward aspects of escalation are only part of the equation. You must also bring the appropriate “energy” to the date to create that magical polarisation of sexual attraction. This is not something you can do on the spur of the moment, but rather comes from the deliberate cultivation of your best masculine qualities. Read more here:
Whether or not the second date leads to intimacy is entirely down to yours and her values, beliefs, and chemistry. Rather than aiming for sexual intimacy as the measure of success for this date, you might be better served by aiming to foster an unmistakable sense of sexual tension between you.
How Quickly Should You Move?
This question is really about how much time a woman is willing to invest in getting to know you before a relationship escalates to intimacy. This will vary according local customs and demographics. The instant gratification of hookup culture has led some people to expect sex by the second or third date, but there are still plenty of men and women with more traditional values who prefer to avoid rushing into the emotional turmoil of an intimate relationship that lacks a solid foundation. In this group, you are also likely to encounter “rules” about how quickly a woman is willing to escalate so as to avoid the social stigma of being seen as “easy”.
The most important aspect to focus on is the feeling you are creating. If you’re interested in pursuing the relationship, by the third date she should have no doubt that you want her, even if you’ve still not escalated all the way to physical intimacy. Also bear in mind that touch and kissing represents a significant intimacy milestone for many people, and if you haven’t at least consistently attempted escalation within the first few dates, you run the risk that she either loses interest, or decides that you lack the confidence, ability, or desire to progress the relationship further.
Advanced Skills: Applying Logistics to Optimise Dating Efficiency
We previously touched on the “hack” of changing venues to accelerate building rapport and trust. If you take this into account when planning a date, you can set yourself up for maximum success by choosing activities and venues that are suitably close to secondary venues. Depending on how the initial part of the date unfolds you can decide in the moment whether or not to suggest the follow-on to the next venue. (This is important: don’t suggest multi-venue dates up front for the first few dates because it makes the date seem a “big deal”. It’s much easier to start with a simple catch-up over coffee, and if the vibe is right pivot to visiting the amazing cocktail lounge around the corner, than to get a near-stranger to commit to both activities up front).
You should also pay attention to logistics when it comes time to escalate intimacy. Almost everyone dates with the expectation that the relationship will culminate at some point in sexual intimacy. The main variable is the speed at which we progress, which comes down to personal values, the confidence and proficiency of the participants to escalate, and lastly the opportunity to consummate.
Depending on your date’s attitude to sex, you may need to provide her with a plausible excuse to come to your home alone with you. Most women don’t want to be seen as “easy” by you or their friends, so it’s up to you to help her feel comfortable with her decisions if you want to move things towards intimacy. Depending on how long you’ve been dating, this might be about providing an excuse for an impromptu visit home, or you could even plan a (non-sexual) activity that takes place in your home. For example:
Have your date meet you at your house so you can travel to a date in the same car. This way you both have to come back to your house afterwards, and you can invite her in for tea/coffee/check out your amazing album collection/whatever justification works!
As above, but pick her up at her house. This puts the onus on her to initiate by inviting you in to her home, but you can always try the “can you invite me in for a coffee before I have to drive home?”
Invite her to stop by your place to meet your dog/cat/goldfish/pet rock.
Once you’ve passed the initial “getting to know you” phase, you can plan a date where you get together to cook a meal, play a game, listen to music, or literally any activity that justifies being alone together in your home to overcome the stigma that she’s going to a man’s house just for sex.
On the other hand, if you share an openness towards sex and you’ve built sufficient tension between you, you can bypass the pretense and get straight down to business!
Gifts and Dating
Men and women often question whether it is appropriate to give flowers or gifts on a date. After all, “gifts” are one of the “Love Languages”, so it’s only natural that some of us want to give or receive these things during the courtship process.
My advice is to follow your own values on this, subject to the following considerations:
Avoid giving gifts of significant monetary value until you move past the dating phase into an established relationship
Instead of a bouquet of flowers, consider giving a single flower. It’s a meaningful gesture, and she can more easily carry or even wear it rather than having to lug around a whole bouquet for the day.
Think about how the gift might be construed:
does it create too much pressure too soon?
does it feel like love-bombing?
does it feel coercive, or like you would expect something in return?
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