Choosing the wrong guys

That Feeling When You Know a Date Isn’t Right Within 5 Minutes

We've all been there—that feeling when you sit down on a date and within just five minutes, you know it’s not for you. You feel frustrated that you put in all this effort, only to realize it’s so far off the mark. It’s disappointing, and possibly even offensive, that someone thought this was the right match for you. Then you get home, feeling exhausted, depressed, and swearing off dating forever.

Does this sound familiar?

5 Reasons Why Your Dates Keep Failing

Here are 5 reasons why this might keep happening:

  1. You Aren’t Clear About What You Truly Want
    If you’re unsure about what you want in a partner, it’s easy to end up with dates that don’t align with your values. Being too ‘open’ can lead to vague expectations like wanting a nice guy with good middos (character), but without specifics, you might get set up with any Jo Shmo.

  2. You’re Not Articulating What You’re Looking For
    Even if you know what you want, you might not be communicating it clearly. Maybe you’re worried about being judged, or you think your preferences will be frowned upon. This lack of clear communication leads to generic suggestions that don’t suit you.

  3. You Say Yes to Please Others
    Are you a people pleaser? You might find it hard to say no, even when you know the match isn’t right. While it’s tempting to avoid disappointment, saying yes when you should say no can lead to resentment, despair, and eventually burnout. Remember, you don’t owe anyone a yes.

  4. You Don’t Feel Worthy of the Amazing Partner You Desire
    Sometimes, not feeling worthy inside can lead to others suggesting partners who don’t match your standards. Mishlei 27:19 says, “As in water, face reflects a face, so too is the heart of a man to a man” (כַּמַּיִם הַפָּנִ֣ים לַפָּנִ֑ים כֵּ֤ן לֵֽב־הָ֜אָדָ֗ם לָאָדָֽם:). If you don’t feel good enough for the man you admire, this belief may subconsciously close you off to high-quality partners. Others pick up on this, suggesting people who match what you subconsciously believe you deserve.

  5. You Have Childhood Wounds That Lead to Self-Sabotage
    Fear of rejection     can cause you to attract partners you can easily reject first. Dating men who aren’t in your ballpark might feel ‘safe’ because you know it’s unlikely you’ll be rejected. This is the ultimate self-sabotage.

How to Stop Repeating Dating Mistakes

What’s the Answer?

Identify which of these reasons resonates with you and take steps toward healing.

Work with Me

Learn more about what we do here at the Inner Circle coaching, therapy, courses, matchmakers! HERE

Jackie Engel