Dating Smart - Communicating, Connecting & Evaluating

As this is the second post in a three-post series, let's recap what we've captured so far. In the first post, we explored individual foundations for discovering where you need to grow and evolve to become the partner you desire to be and how to approach dating with intentionality. This is important for two reasons, 1) to make sure you are approaching dating from a healed, balanced and purposeful place and 2) because it is crucial to understand how you connect with others to maximize success in pursuit. Ultimately, when you know better, you do better, thus, make every effort to ensure that you understand what is hindering you from achieving your dating goals, and having successful relationships. And this includes understanding whether or not you're allowing prior relationships to influence how you approach dating with purpose and intention.

Additionally, when engaging with or dating others, the engagements should be mutual beneficial. Approaching dating in a purely self-serving (selfish) way, focused only on meeting your own needs, does not create a positive experience for the other person and can become toxic for all parties. Thus, it is always essential to do the self-work to approach dating from the right space, and where concerns are identified, make sure to actively work on making adjustments, for the better. It is also equally important to ensure dating efforts and perspective are aligned with your dating goals at all times.

Now, hoping you've had a chance to read the first post, evaluate your history, and set dating goals, let's uncover how to evaluate partners in a way that ensures authentic connection with compatibility. This will include a review of the importance of honest communication, identifying and understanding the qualities that you seek in a partner and remaining true to that pursuit.

DATING THROUGH HONEST COMMUNICATION

Dating with intention first requires transparency with yourself and with others. And that is because honest communication must be intentional. Therefore, transparency is intentional. So, it's important to know the difference between being honest intentionally, and being honest reluctantly.

Reluctant honestly is used by those who have no choice but to be honest, and that's a red flag. That signals that if they had the choice, they'd likely prefer to either withhold or omit the truth. And in some instances they may even prefer lying. In short, being forced to be honest and choosing to be honest are very different things.

Noting this, however, what typically remains unclear is how to determine whether honest communication it's being reciprocated. Reluctant honesty simply can be addressed by asking "Is there a particular reason you don't want to discuss ____________." This will confirm whether they are holding back but also provide explanation of reluctance.

Furthermore, it's easy to think just because you say what you want and someone agrees with everything that you all are aligned.

IMPORTANT NOTE: Frequent agreement without individual perspective illustrates potential for communication and perception issues that may hinder successfully achieving dating goals. And that is because agreement does not represent compatibility. Compatibility is more about having sharing goals, values and willingness to respect, understand and work through differences. Whereas agreeing (or agreement) is very surface and represents a simple choice to concede. In short, compatibility understands degrees of difference while pursuing shared goals.

The real challenge often lies in evaluating who truly aligns with your values, goals, and long-term vision. And the intentionality of dating rests in making conscious choices to end pursuits or connections that do not align with identified goals, values and vision or positively impact you. Let's now review how to evaluate a suitable partner and develop healthy dating habits. Habits that enable healthy communication, connection, and proper evaluation.

MASTERING EVALUATION IN DATING

I. EVALUATING DATING MOTIVATION & INTENTION

Many relationships fail simply because the other person did not listen or acknowledge that they were engaging with someone who was not aligned with their long-term goals.

Evaluating dating motivation and intention is the first step in evaluating the success of any partnership. So, it's important to LISTEN! And while conversations or exchanges may be uncomfortable, it is important to ACCEPT what the other person says. For example, if you share that your dating goal is marriage, but the other individual is seeking a friendship, the response would be to acknowledge that you are not in the same space and thank them for the time you've shared thus far. At that point, there should be a mutual understanding that there is no alignment with long-term goals, and therefore, the connection will ultimately fail to thrive. Recognizing and accepting in the beginning that dating motivation and intention are not aligned, allows you to more easily recognize common red flags, such as the failure of one party to define the connection, lack of follow-through, and inconsistent communication.

Try not to focus too much on the physical connection in the most critical stage of dating (the beginning). Especially when in the beginning people are generally open and willing to learn more about the other, to understand best ways to connect moving forward. Therefore, take advantage of this time. Make sure you are asking the right questions and paying attention to all the red flags from the start.

So what about potential? Evaluating and honoring someones' potential has no place in proper evaluation, because when evaluating where someone is, they have to present that way at the time of the evaluation. In other words, what you see is what you get. Hoping and wishing for preferred traits to appear should not be used to justify alignment with long term partnership or dating goals.

II. ASKING THE RIGHT QUESTIONS!

Often individuals are challenged by truly understanding how to connect with and learn about others. The first step in evaluation is to make sure you're asking questions that help uncover alignment with dating goals, long term life goals, family and life values, emotional maturity and stability, patterns of behavior and lifestyle choices.

Here are some example questions to help support the dating journey.

1. What does a "good life" look life for you?

2. What core beliefs and family values that are most important to you?

3. What life lesson or experienced shaped or most influenced by who you are today?

4. How important is spirituality/purpose in your life?

5. What does marriage/long term partnership look like to you?

6. How do you handle stress, disagreements or conflict?

7. What is your definition of cheating or infidelity?

8. How does someone lose your trust?

9. How big is trust to you in a relationship?

10. What are your strengths and weaknesses?

11. How do you navigate daily challenges?

12. How much alone time do you need and why is that important to you?

13. What are your passions, hobbies or projects outside of relationships that you like to maintain?

14. What does self-care look like to you?

15. What do you value most in a romantic relationship?

16. How do you show love and affection?

What about Finances & Politics? Some believe that politics and finances should be a part of the discussion in the beginning stages of dating. However, I would NOT advise addressing these topics in the beginning. That is because indirectly these items present. As they present themselves, you can determine whether your connection is worth working through or accepting any differences and determining whether the differences are irreconcilable at that time.

But, as connections grow, you naturally learn more of the "why" behind their feelings on politics and finances. You may also find that you come to accept or choose to shift your own beliefs. So, there's no need to create issues before you determine whether the individual you are pursuing is worth acceptance and compromise.

Also, notice that love language has not been included in the discussion thus far. And that is because love languages are NOT used to determine who you are compatible with. Love languages are expressions of love and therefore do not help determine if you and someone else are compatible. When you love someone, you will love them in the way they receive love, and visa versa. Therefore, the use of love languages essentially illustrate the extent of love you hold for another, but it does not and should not be used as a determinant of compatibility.

Ultimately, you want to make sure you understand where the individual is on their personal growth journey, how their independence impacts how they connect in relationships, the role that family plays in their life and in their relationships (e.g. how important is family in the process), and how their individual goals and spiritual path influence how they connect with others and show up in relationships. And while this should go without saying, you certainly need to understand these aspects of your individual journey to be able to communicate them to your person of interest and also evaluate alignment.

This section is designed to support an ability to evaluate whether someone truly aligns with one's desires and can show up in a connection as desired. It is also important to recognize that differences can exist in healthy relationships, so do confuse compatibility with only seeking someone that sees the world exactly as you do.

III. FIVE KEY CONSIDERATIONS WHEN EVALUATING

While there can be more, in evaluation it is important for you to know what you are seeking in order to determine/evaluate who aligns with your goals. Here are 5 key considerations that help you determine whether someone aligns with your dating goals.

1. Non-Negotiable's - Immediately discontinue pursuing anyone who meets your non-negotiable.

2. Observe their communication style! - Pay attention to how they communicate. Are they being transparent, honest or clear? Are they reluctantly honest or holding back? Do they have clear insight of their personal goals?

3. How do they argue? - Arguing in relationships is likely inevitable whether a large or small disagreement, the key is to understand HOW that individual addresses conflict. Are they empathetic, compassionate, a great listener and open to agreeing to disagree? The positive response would be a green flag where emotional outbursts, cursing/yelling, lack of control or dismissiveness, etc. would be a red flags.

4. Emotional Availability, Trust & Loyalty - Emotionally available partners share their inner world and make space for yours, allowing vulnerability, honesty, and mutual support. They don’t avoid intimacy or shut down during hard moments. Through consistent actions, keeping commitments, telling the truth, and respecting boundaries, they build trust over time. Loyalty shows in how they speak about you, stand by you in challenges, and choose the relationship through steady, reliable commitment.

5. Independence & Healthy Boundaries - A healthy partner keeps their own identity, friendships, and interests while respecting yours. They don’t expect you to meet all their emotional needs or control your choices. Instead, they respect boundaries, can say no, honor your limits, and support your independence and relationships.

DISCLAIMER: If your goal is a romantic relationship, choosing to remain “just friends” with someone who has made it clear they only want friendship does not align with that goal. Thus, remaining friends can blur boundaries, prolong attraction with others, and create emotional complications, because simply agreeing to friendship doesn’t eliminate desire or attachment. So, maintaining that connection while dating others can be confusing or negatively perceived. In many cases, it sets you up for unnecessary frustration rather than clarity.

For example, explaining that friendship will inevitably become difficult, especially to someone you’re actively pursuing. Over time, they may conclude that the only reason you are not with that friend is a mismatch around marriage, not a lack of attraction or compatibility. To them, it sounds like, “If marriage were possible, they’d be with them, not me,” which creates unnecessary insecurity.

If your true goal is a romantic relationship and someone clearly doesn’t align with that, maintaining the relationship serves little purpose. It often leads to disappointment, as the friendship can quietly fuel hope that the dynamic will change, despite already knowing misalignment is present.

RECOGNIZING RED FLAGS

Naturally when getting to know someone, it's important to recognize and acknowledge red flags as they present in your connection. This process is valuable for many reasons, but primarily it is an indicator of your personal growth.

Common red flags include inconsistency, avoidance, emotional immaturity, lack of accountability, disrespect, lack of regard for established boundaries and need for constant validation. The rate at which these are viewed significant will vary by individual growth journeys, however, it's important to recognize that these red flags warn you of existing or future challenges and issues. Therefore, it is best to recognize them and address them as they arise.

Also, depending on where the connection is, recognizing and addressing red flags may prompt greater discussion and intimacy through tough (but necessary) conversations. While I will not provide guidance on how to address red flags, because I will leave that to the reader's discretion, my only suggestion would be to give individuals the chance to correct the behavior if they choose. For those who choose not to make changes to negative behavior, it is then a question of 1) changes in compatibility or 2) whether the individual no longer aligns with your dating goals and the connection you seek. Re-evaluate to determine if you need to move on from the connection.

BUILDING CONNECTIONS THROUGH AUTHENTICITY

It's very healthy when dating to continue to check-in with the other party and make sure that you both are still in pursuit of the same goals and vision for future interactions. In the first post I discussed five types of daters that are most often encountered. To provide a brief recap, the most common types of connections pursued when dating are friendship, physical, emotional, similarity/compatibility and experience.

More specifically, friendship daters need trust, warmth, and platonic bonding before romance can grow, physical daters feels most connected when there’s an early spark, flirtation, or physical intimacy/attraction, whereas emotional daters form bonds by sharing emotions, personal stories, and deep dialogue. Similarity/Compatibility daters feel closeness when long-term fit, structure, and mutual direction are clear and experience daters build connection through playfulness, shared moments, and doing things together.

This is important to understand because experienced daters or those intentionally seeking marriage or long-term partnership, approach from the space of experience, friendship and/or compatibility first and then later connect physically or emotionally. Therefore, ensuring that you are being mindful of what benefits your dating goals will keep you authentic in your dating pursuits. Ultimately, authentic connections require open communication about where you are, and follow-up as your needs shift to facilitate a genuine connection with someone. Active effort and intention are required from both parties to ensure an overall positive dating experience for everyone.

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