dating coaching

Valentine's Day First Date Tips

Tips to be a good first date
….and to have a good first date. 

Typically dating life begins to pick up in the new year, as the days get longer and everyone's New Years resolutions kick in. By February, with Valentine's Day just around the corner, singles everywhere start to tune back in to their heart's desire for a partner. This may be part of an evolutionary drive if we are anything like our winged friends---During the Middle Ages, it was commonly believed that February 14 was the beginning of birds' mating season, which may have been part of the reason for the romantic associations with Valentine's Day.  Whatever the reason for this renewed interest in dating and romance, when it's been awhile since our last bout of dating, it can feel nerve-wracking to go on a first date. Already this month, I've had several different clients and potential matches come to me with the first date jitters. In light of that, and in light of finding new love in 2017, the year of the fire rooster (or the "red cock" as my dear friend and relationship astrologer Rebecca likes to call it), I decided to write up some tips that I find useful for clients in easing their nerves and having success on first dates. Below I've included a guidebook to a first date that is geared towards BEING a good first date in order to have a good first date, one that you can reference when you find yourself trembling with those first date jitters. Here goes...

When getting ready,
Set your expectations to zero.

Expectations are tricky things. They creep up on us like a panther in the jungle and before we know it, we’ve judged our date for their shoes and hoodie, the way they fumbled, laughed too loud, or called us by the wrong name. Sometimes we’ve written them off completely by the time we sit down to talk and they are struggling to find ways to engage us. It’s easy to look back and say, “that reaction wasn’t caused by my expectations, that reaction was caused by THAT PERSON.”  In truth, our reaction tells us more about ourselves than it does about the person we are with.

The thing about expectations is that they are a classic double-edged sword -- they protect us from getting disappointed but they also set us up for disappointment.  That disappointment spells disaster when it comes to actually getting to know the person sitting across from you on your first date. And, after all, getting to know someone is the foundation of dating.

It’s actually a harmful thing to do to judge a person because they aren’t what you want. A better approach is to have a peptalk with yourself. Say to yourself: “okay, let me make the most of my time with this person, see in what ways I can learn and grow, and end the date when it’s time to end the date.” We tend to forget that relationships don’t develop instantly.  I can assure you that they don’t, and if they are to last, change, evolve, and grow--in short, if they are to become healthy lasting relationships - it’s important to keep in mind that good things evolve over time.

When you’re walking up to the date,
Channel excitement, enchantment and curiosity.

past tense: enchanted; past participle: enchanted
  1. fill (someone) with great delight; charm.
  2. "Isabel was enchanted with the idea"
  3. Captivate, charm, delight, enrapture, entrance, enthrall, beguile, bewitch, spellbind, fascinate, hypnotize, mesmerize, rivet, grip, transfix
  4. put (someone or something) under a spell."an enchanted garden"

Allow yourself to be enchanted and curious about the person that you are about to meet. Let yourself be excited whether your date looks like their photo or whether they are completely different than who you’d consider conventionally attractive. There’s nothing worse than seeing your date’s face fall a little when they see you.  So put out the energy you want to get back, and just let yourself be excited to meet this person. Each person (including yourself) is like a gift, and our appearance is just the wrapping paper. You never know if they’ll be a good friend, a business contact, or someone you end up dating. First impressions are important and we can never change our first impression--so make this first impression intentional and enchanted!

On the date,
Keep the focus on how you feel, AND don’t be afraid to say it!

Keep taking your own “feeling” temperature. Ask yourself how things make you feel, and don’t be afraid to express it. I.e. if your date says something you like or that makes you happy, say “Oh! That makes me happy!” If your date starts making comments that make you feel uncomfortable, say “I feel uncomfortable.” If your date, says ‘I know our reservation is for inside but the patio looks nice,’ and to you the patio looks too crowded, say “The patio looks a little crowded, which might make it hard for me to hear you. I’d prefer inside.” One side note with this tip - no matter what you are saying, say it in a way that is about expressing yourself, not making the other person wrong!

Your voice is important, and if your date is “the one” for you, they will appreciate hearing how you feel and what you have to say.  Give them that chance.

When in doubt,
Ask questions.

Going on dates can be hard, especially if you’re shy or not big into small talk.  When I was younger and pretty shy myself, I took some of my dad’s advice. He too, was shy when in his teens and twenties, and always advised me “Ask people questions about their life. It makes them feel good to tell you about themselves and it takes the focus off of you.”  I know this is true, because I experience it when someone asks me questions - their interest feels good and I like answering questions. In fact, it’s easy to answer questions about myself because that’s the subject I know best. I can’t even begin to tell you what good advice this is when it comes to dating.

The art of asking questions itself is a creative and engaging act, and allows both parties to feel engaged and interested. Questions open up new territory and allow us to get to know one another more deeply. If you’ve heard of, or perhaps have tried, the 36 questions by Arthur Aron, you have a sense of what I’m talking about. The added bonus of asking lots of questions is that you can discover whether the person across from you is actually compatible with you!

My advice to those who like to prepare is: come up with a few questions ahead of time that you can pull out of your back pocket in a pinch (you can borrow from the 36 questions or from the list below.) And for those who don’t go in prepared, think of conjuring up questions as a creative exercise for your mind.

Here are a few creative questions to spark your creativity (use only those that apply!):

1. What do you love about your job?
2. What’s been the best part of your day so far?
3. What’s on your mind today/this week?
4. How’s your favorite sports star/team faring this season?
5. What’s your big adventure going to be this year?
6. What’s stopping you?
7. What do you love to do when you’re all alone?
8. How would you like to move forward on [name a particular project]?
9. What’s your idea of a perfect day?
10. What makes a man/woman approachable?
11. Tell me about one of your role models growing up.
12. Which holiday do you dread most? Why?
13. How do you relax? (Or, What do you do for fun?)
14. If you could change just one thing about your life, what would you
15. Tell me about one of your childhood friends.
16. What do you think is different about older women?
17. What makes someone really good to work with?
18. Have you ever been in a really dangerous situation?
19. On a scale of 1 (awful) to 10 (awesome), what did you think about ….?
20. What particular obstacles are between you and your best future
right now?
21. Tell me what insights you’re gaining by being in that particular
22. What do female friends give you that you just don’t get from your
male friends?
23. What’s something you typically avoid?
24. If you could have one super-power, what would it be?
25. What’s missing from the picture so far?
26. What surprised you about ?
27. What makes you feel free?
28. Tell me what’s awesome about being a man/woman.
29. Who are some of your heroes?
30. If you could live anywhere in the world, where would you live?
31. Tell me about something you’re incredibly proud of.
32. How much “alone time” do you typically like to have? How do you
make sure you get it?
33. If you could see any band (living or dead, together or not), who
would you love most to see?

After the date,
Bring the focus back to yourself.

It’s so easy to get caught up in “did he/she like me?,” but ask yourself, “Did I feel good around them?” Did I like them? Why or why not? And keep the focus here. Journal or write about it on your computer or Evernote or calendar. If you’re not much of a writer, simply take time to reflect on this central question of how you feel around the person. Anytime you notice yourself starting to wonder “What are they thinking about me?” or you feel that old familiar feeling of rejection (“why doesn’t anyone like me”) or arrogance (“they like me, but I’m not into them”), your ego is getting in the way of the experience of true connection. Now, egos aren’t inherently a bad thing, but they do keep us from feeling all those feelings of connection we are seeking in a relationship.  So remember this: when you start to focus on the other person, you are distracting yourself from what is most important in a relationship - which is how you yourself feel, relate, and are supported, AND you are directly inhibiting the process of falling in love and creating deeper connection.

So, this month when you're going on first dates, remember:
-Set your expectations to zero
-Channel excitement
-Say how you feel
-Ask questions
-Keep the focus on yourself and how YOU feel

Good luck out there :)  

A romantic song for the month: 
Dust to Dust

Frequently Asked Questions

Q. Is having expectations from your partner a good thing or a bad thing?

A. Bad expectations are when you have an idea of what your partner should be like, but they don't match up with your expectations. You might think that having high expectations is a good thing, but it can lead to disappointment and resentment. Good expectations are when you have realistic expectations and you're able to accept that people change over time. Your partner will grow with you as long as you communicate with them and work together. 

Q. What are the qualities of a healthy relationship?

A. A healthy relationship involves both parties feeling like they are being heard and understood by the other person. A healthy relationship has some give-and-take where each partner respects the other enough to not always have their own way. 

Q. What are some signs of a healthy relationship?

A. Relationships are not easy to manage. It takes a lot of time, patience and effort to maintain a healthy relationship. But it’s worth it! A healthy relationship is characterised by mutual respect, empathy, understanding and love between the partners. 


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