First Dates — Helping you Avoid the Fails and Create Space for Success

Hello Singles

Today I am diving into the topic of first dates, specifically those that have begun on dating apps. As with all of my articles, my suggestions are for those of you authentically looking for meaningful connection and a relationship that progresses over time. I speak from my own perspective and experience as a 50+ woman which you can take or leave, as you wish. Feel free to comment below.

Be intentional right from the beginning

Why? Because this might be the start of your story together — make it a good one. If you need some first-date inspiration, ask the couples around you what their origin stories are; listen to those of your parents’ generation. There are some beautiful beginnings out there.

The Pre-date Date

Often, there is a prequel to a date, especially if you haven’t had longish video or phone conversations. This might take the form of meeting for coffee or a walk (or a walk with a coffee!). Something brief and low-key to test the waters. If after this encounter, you find yourself thinking about the person, how it went, feeling curious about what is next, then maybe a romantic date is in the cards.

If it felt like a job interview — even if all the needs/wants boxes are ticked —be respectful and communicative, but move on.

If it is clear, they are looking for a hook-up (and you are not), or if they are not the person you signed up for (kitten fished), full stop. Be the ghost.

Invest yourself and your time in what you desire, not what you are offered.

Having the Feels

It may be that the chemistry and connection during this preliminary get together evolves into something that feels like a date. If this happens, communicate it. Say, “hey, this is going well, would you like to … (insert date suggestions). If your companion is also feeling it, the two of you can create a fun experience together in real time. It highlights spontaneity, and if this is a trait you value, awesome and congrats!

Not to put a damper on your first date win, but, I do think there is value in putting a little time and space between each of these early encounters. Longterm, it might serve you better — both of you. You know that if/when the next date occurs, and the next, it is because everyone chooses to be there…again it is about intention.

In-Person First Dates

If you are dating within your city or region, you have a multitude of options for your first face-to-face. The nature of your choice will depend on how long you have been interacting (messages, video) prior to that first “official” date, and how much you have already learned about the other person — their passions, expectations, and needs.

What and Where

Choose an option that involves a shared experience. Something based around personal interests or a special event. Outdoor activities are generally a good plan; you can never go wrong with a picnic in a nice quiet spot in my humble opinion. (Be sure to know their food preferences prior to packing).

The goal is to find a low-pressure and organic way of getting to know this new someone. Going to a movie where you both stare straight ahead can be awkward. If this is your go-to, I suggest a post-movie follow-on like a walk or quiet café where you can converse. The idea is not merely spending time together but progressing the level of connection. You need to be talking.

If you have already interacted virtually quite a bit, a dinner out, or listening to live music can be a great choice. You are already comfortable conversing so get out there and experience each other in public settings that involve external interactions…and are fun.

Getting there

For comfort/safety reasons, for a first encounter, women often prefer to meet at the destination, or near it. This is a sad state of affairs, but often a practical reality. Anyone who takes offence to this, should be metaphorically, swiped left.

Timing

A friend brought this to my attention recently and I think this is a good approach. Consider having the first date during the daytime. One that begins in the evening possibly carries with it the hope/expectation of a “night cap”. Depending on your comfort zone in this sphere, anxiety around this might colour your experience of the evening right from the get-go.

Presentation — Men

Oh boy, do some of you need help! I spent 9 months on dating apps when I lived in Canada and went on 20 or so in-person micro-dates …. almost all the men showed up in overly casual clothing….T-shirts, logo’d sweatshirts, running shoes. If you actually want to impress, dress like an adult. Think business casual, not grocery-getter, or soccer dad. No baseball caps please!

My personal read on a haphazard clothing/presentation style is, “I was in the neighbourhood and the timing for coffee worked with my schedule”, “I do not want you to think I am too interested in you”, or “I couldn’t be bothered since it is just a coffee meet”. It suggests that finding/exploring relationships is not a very significant priority after all, and you do not care whether we like you or not. So, refresh my memory why are we meeting?

Presentation — Women

Often, women tend to skew towards the other end of the spectrum, giving too much thought to what their outward appearance is and not enough to expressing their authentic self. Do not dress like you are headed to a party or a night of dancing (unless you are). Wear colours and clothes that give you a boost and you feel good in.

If your personal style exudes sexiness, be mindful of this superpower. While it may not infer anything from your perspective, my cautionary message is that you do not know this person yet, nor their expectations; maybe save a little for the second date.

My overall comment to all the genders is to

be You — the best You.

Quality attracts quality.

Long-Distance

When you are beginning a relationship from a distance, the first date will necessarily be a little different, but I think it should still be understood by both of you as a “date”.

Dress codes and intention still apply. This may be the beginning of your story together, it matters.

For a first date, each of you with a glass of wine (or a coffee) and an open-ended time commitment is a simple but very pleasant beginning.

Lack of direct physical connection is certainly challenging but knowing when an in-person date will occur, helps and the planning of said encounter is fun and cooperative. If the relationship changes/ends before you get to the in-person meet, c’est la vie!

I will write about this in a future article, but keep in mind, with a long-distance relationship, there does need to be an end-game strategy. When will you eventually occupy the same space? Or will you? Where will it be?Discuss this openly and early-on so that expectations (and hopes) are clear.

Dating fails

There can be a big difference between online and in-person chemistry, and who can really understand or explain either. Sometimes (maybe often), that first in-person date will not be the date of your dreams. It might even be awful. It is okay. Odds are you learned something: about yourself, about what you need, or about your approach.

I promise there are many amazing partners and experiences out there, and by letting go of one that did not work, you open the door for another that will.

Show up. Stay in the moment. Have fun.

Talk soon,

Karen

https://karenespig.medium.com/membership

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This post was previously published on medium.com.

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