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DateWell

Dating, but easier.
Because when you understand yourself, everything gets easier.

Dating feeling like a struggle and not sure why? We’ve got a fun, simple way to uncover what’s really going on beneath the surface of your dating life. Check out our Dating Types and if you think “That’s so me!” dive deeper for more insight!

Identify your type. Get insight. Date wiser.

Behold a lighthearted and engaging way to uncover what’s really going on beneath the surface of your shidduch journey. It features twenty characters, each reflecting a different personality and dating experience. The goal is to help you to better understand yourself and your dating. 

The So-Me Dating Types are short, spot-on profiles that capture how different people actually show up while dating. If one makes you think, “That’s so me,” you’re in the right place. Dive deeper to uncover what’s driving your experience — and date with more clarity, confidence, and intention.  

Some of the So-Me Dating Types may feel similar on the surface, especially in how people show up on a date. For example, two types might both struggle to open up or share about themselves — yet for very different inner reasons. You may find that more than one type resonates. Read with curiosity, notice the nuances, and see which one feels most true when you’re being really honest with yourself.


 

Chaim has been dating for a couple of years and has had a number of shidduchim. Quite a few went on for a while, and seemed for a time to have real potential. In the end, though, Chaim felt unable to continue. Most of the shidduchim ended because Chaim felt stressed, uneasy, and very stuck. But why, after so many promising starts, did things fall down?

Chaim discovered our “That’s so me!” hoping to get some insight. At first, he came across Anxious Abigail and found parts of her story familiar—the stress, the emotional drain, the sense of overwhelm. “Maybe that’s me,” he thought. “I do get really anxious when I date.” But something didn’t sit right. “I’m not usually an anxious person,” he realized. While some of it resonated, it didn’t quite capture the full picture—so he kept looking.

Chaim was drawn to Commitment-Phobic Connie. “That sounds a lot like me,” he thought. “Dating feels easier at the beginning, but I tend to pull away after a few dates. Maybe this is me?” he wondered. But again, he wasn’t sure, as he didn’t experience the kind of panic that often comes with this type, nor the typical strong sense that something was wrong.

When Chaim met Indecisive Izzy, the penny dropped. “That’s so spot on—it describes me to a tee,” he said. “I get stuck for no clear reason. I make endless pros and cons lists, talk everything through with people… and still don’t move forward.” What really hit home was the part about how the indecisive type sometimes sabotages the relationship just to avoid making a decision—and then feels relief when it ends. “That’s exactly what’s happened to me so many times,” Chaim realized.

That realization brought a wave of relief. “Clearly, I’m not the only one experiencing this,” Chaim said. He felt seen and understood. “It seems what I’ve been going through is a real thing.”

Encouraged by the clarity, Chaim clicked through to explore more. He found helpful content that explained how indecision can show up in dating, along with some initial tools for moving past the constant paralysis. Inspired by this new insight, he sought advice from a coach about how to avoid his indecision from calling the shots.

Maybe you’ll find your “That’s So Me” here—and suddenly, things will start making sense, giving you the insight you need to move forward.

Take a look at all the characters, or focus on the question/category that most resonates with you. You can also check through all if you’d like a full view.

SO-ME CATEGORIES FILTER
  • All
  • Decisions Struggles: Do you struggle with making choices, overthinking, or worrying? (6)
  • Emotional Connection Issues: Do you struggle to connect, trust, or get close to others? (5)
  • Feeling mismatched: Do you find it hard to feel truly matched with the people who are suggested or whom you date? (5)
  • Communication / Dating Skills: Do you feel like you could use a little more guidance in navigating dating or expressing yourself? (4)
  • Too quick attachments: Do you feel intensely about your date — sometimes too quickly? (3)

Worrier Willy

“I tend to be endlessly fearful that something could go wrong or will go wrong.”

Worrier Willy

  • Is endlessly concerned about bad outcomes
  • No reassurance lasts long or is ever enough
  • Expects negative outcomes
  • Fixates on issues between dates
  • Small issues become overblown
  • Too worried to enjoy the process
  • Often assumes something is wrong with shidduch

Click for more

Anxious Abigail

“I'm constantly feeling nervous, especially between dates, and usually can’t figure out why.”

Anxious Abigail

  • Finds dating overwhelming and emotionally draining
  • Experiences extreme stress leading up to or during dates
  • Often doesn’t enjoy the process, even when things go okay
  • Tends to mentally shut down

Click for more

Obsessive Odelia

“I go all-in emotionally very fast, and get attached before I actually know the other.”

Obsessive Odelia

  • Gets attached emotionally super quickly
  • Overshares personal details or deep feelings prematurely
  • Wants to be in constant contact
  • Worries a lot that relationship will end
  • Looks for relationship to progress fast
  • Heartbroken if shidduch ends—even if it was just a few dates

Click for more

Tongue-Tied Tony

“I just can’t seem to find the right words when I need them. Communication doesn’t come easy, especially feeling under pressure.”

Tongue-Tied Tony

  • Lack of verbal skills
  • Feels overwhelmed when putting thoughts into words
  • Long pauses, vague responses, or deflecting questions
  • Often quiet or minimal input to conversations
  • May seem emotionally distant, though they’re not
  • Worries about saying the wrong thing
  • Hesitates by which time opportunity passed
  • Typically feels stuck when it’s time to share something personal

Click for more

Commitment-phobic Connie

“Things seem to go well … until the relationship starts to get serious.”

Commitment-phobic Connie

  • Struggles when the relationship gets serious
  • Invents minimal justifications to end shidduch
  • Experiences panic and dread dread about moving toward
  • Is convinced something must be wrong
  • Almost never feels ready to get engaged
  • Pulls away even after weeks of positive dating

Click for more

Detached Dan

“I like her on paper… but I’m just not feeling it.”

Detached Dan

  • Struggles to feel an emotional connection, even after multiple dates
  • Feels close to family/friends, but not dates
  • Breaks off dates even without fault
  • Uncomfortable or awkward receiving affection
  • Often, unclear how emotional connection should feel 
  • Even when things go right, still feels little or no emotion

Click for more

Overthinking Ollie

“How can I be sure this is the right person for me?”

Overthinking Ollie

  • Persistent uncertainty regardless of how many dates
  • Relentless second-guessing and self-questioning
  • No evidence or reason is ever sufficient to settle an issue
  • Often looks to buy more time to avoid making decision
  • Would rather walk away over making a decision
  • Fear making the wrong choice more than missing a good relationship
  • Highly unlikely to trust their gut feeling

Click for more

Fixated Fernando

“Looks really matter to me—If only s/he were more attractive, this would be perfect. I wish I could get past this, but I just can’t.”

Fixated Fernando

  • Fixates on one surface aspect—appearance, income, height, etc.
  • Ends shidduchim quickly despite everything else going well
  • Attributes discomfort to the other's "not enough-ness"
  • Secretly hopes external qualities will override internal barriers
  • Hopes excitement will rescue them from own ambivalence
  • Finds commitment difficult, but doesn’t consciously connect the dots

Click for more

Ambivalent Avram

“I'd really like it to work, but something is holding me back. It’s not a no—it’s also not a yes either.”

Ambivalent Avram

  • Avoids emotional depth, keeps conversations superficial
  • Often has many short shidduchim that don’t progress
  • Often warm and charming—but at times indifferent and apathetic
  • May disappear for stretches or prioritize other interests
  • Often gives mixed signals: interested one day, distant the next
  • Small issues have an outsized impact of motivation level
  • Uses “not sure” as a shield to avoid vulnerability

Click for more

Perfectionist Pinchas

“If it’s not exactly right, it’s wrong. I just can’t settle for ‘okay. What if there’s someone better out there?”

Perfectionist Pinchas

  • The anxiety of “what if” consumes her dating process
  • Slightest imperfection could be a dealbreaker
  • Feels there’s always something off
  • Tormented by the prospect of someone better out there
  • Ends up scanning for flaws instead of looking for connection
  • Compromise feels more uncomfortable than being alone
  • Accepting anything less than perfection feels like “settling”
  • If there’s even a small imperfection, is convinced won’t be happy

Click for more

Fearful Feivel

"I’m not meeting people who make me feel comfortable."

Fearful Feivel

  • Frequently ends relationships, often after several dates
  • Focuses on what could go wrong, even when dates are going well
  • Is guarded about their emotions / reluctant to become vulnerable
  • Keeps searching for reasons not to move forward
  • Magnifies small concerns into major risks
  • Never feeling ready, always outstanding issues 
  • Highly likely to want to take breaks
  • Brings up issues later on that weren’t an issue before

Click for more

Disappointed Debbie

“Every time I think I found the one, something ruins it. I get excited at first—and then reality sets in.”

Disappointed Debbie

  • Gets  swept up in the potential — then crashes upon seeing a flaw
  • Holds a strong mental checklist of must-haves
  • Feels let down when dates don’t live up to unrealistic early impression
  • Intolerant of normal flaws or inconsistencies
  • Longs for a perfect alignment, and is crushed when reality hits
  • Often compares dates to an idealized vision of a spouse
  • Denies having elevated expectations
  • Likely blames failure on the other’s imperfections

Click for more

Infatuated Ita

“We just met, but I know we’re getting married. Perfect in every way. That's all I could think about.”

Infatuated Ita

  • Gets swept up in intense feelings of admiration and excitement early on
  • Sees the other person through a lens of idealization, focusing on their best qualities
  • Imagines a future together almost immediately, feeling as though everything clicks
  • Has scant interest in the facts and overlooks any red flags or doubts
  • Daydreams about the relationship constantly and struggles to function normally
  • Struggles to keep things in perspective, prioritizing excitement over realistic assessment
  • Tends to feel a sense of urgency to move things forward quickly

Click for more

Indecisive Izzy

“Dating would be great if I didn’t have to make any big decisions. They paralyze and terrify me. Like, what if I make the wrong choice?”

Indecisive Izzy

  • Struggles to move from “neutral” to a decision—even after many dates
  • Makes endless pros and cons lists but still feels stuck
  • Often consults multiple people, but only gets more confused
  • Hesitates to end it or move forward—worries about regret either way
  • Feels pressure to be 100% sure, fearing the weight of lifelong consequences
  • Secretly hopes the other party will end it, so can be put out of their misery
  • Will sometimes actively sabotage the relationship to avoid decision
  • Often feels relieved when shidduch ends, as they avoided a decision

Click for more

Evasive Esther

“I’d rather not get into all that right now… perhaps we can circle back to it later.”

Evasive Esther

  • Avoids deep or personal conversations, keeps things light and casual
  • Frequently redirects conversations away from emotional topics
  • Feels uncomfortable sharing personal details or thoughts
  • Feels anxious or exposed when discussions move toward meaningful connection
  • Worries that revealing too much could lead to judgment or misunderstandings
  • Prefers an easygoing, no-pressure dynamic, and avoids direct questions or serious talks
  • Chronically procrastinates when dealing with matters of a more personal nature

Click for more

Independent Itzik

“I’d get married if it was the right person, but I have a pretty good life being single. If things work out, fine. Otherwise, I'm good on my own.”

Independent Itzik

  • Values personal freedom and self-sufficiency, and is reluctant to surrender them 
  • Often think they don’t need a relationship to feel whole
  • Prioritizes personal goals and interests, and can even resent the need to date
  • If relationship makes too many demands will hold tightly to their independence
  • May push people away when they try to get too close or suggest a deeper connection
  • Struggles to open up emotionally, keeping things at a surface level
  • Is typically less willing to make concessions or adjustments to make it work for other

Click for more

Clueless Kalman

“I try my best and think dates go well, but I keep hearing I’m doing it wrong. Dating feels like a mystery.”

Clueless Kalman

  • May find conversations awkward or hard to keep flowing naturally
  • Dating etiquette is often confusing
  • Could have hard time planning and managing dates
  • Often can’t think of suitable topics for conversation or discussion
  • May struggle to ask meaningful questions or show genuine curiosity
  • Might unintentionally come across as distant or disinterested 
  • Sometimes misses simple social cues or emotional signals
  • May not use first name or not escalate the connection

Click for more

Complex Kayla

“There’s always something that feels off—no matter who I date. Part of me wants this… but another part is screaming no.”

Complex Kayla

  • Has two distinct sides to their character, such as introverted and extroverted
  • Find themselves drawn to very different types of people—none feel quite right
  • Feels pulled in opposing directions, often without fully realizing why
  • May idealize a “perfect fit” who could somehow satisfy both sides of their personality
  • Can appear picky or hard to please, but it’s really an internal tug-of-war
  • Due to low satisfaction is typically certain that their dates aren’t “the one”
  • Often has an extensive history of shorter dating experiences

Click for more

Conflicted Casey

“No matter what I pick, it feels like I’m leaving something important behind. I wonder if I know what I really want.”

Conflicted Casey

  • Whomever they date, they feel that they aren’t being true to a part of themselves
  • Struggles to feel satisfied because of some negative feeling, such as shame or guilt
  • Can be drawn to someone, then feel restless later 
  • Often wants to make a decision, but is left second-guessing with a pit in their stomach
  • Often a struggle between what they think would make them happy versus what they feel is right
  • Often manifests as conflict between what they prefer versus what they were taught or raised to value
  • May flip-flop on what they're looking for, depending on who they're speaking to
  • Often wishes someone else could just tell them what to do

Click for more

Naysayer Noam

"There’s no way that’s for me. It was clear from the first second. What were they even thinking?"

Naysayer Noam

  • Has a tendency to write people off quickly, assuming they're not a good match
  • Feels like every date is with someone who doesn’t fit their ideal or values
  • Often think they’re being misunderstood, frustrated at shadchanim  
  • Gives a hard no, is rarely open to another point of view
  • Feel they’re wasting their time, get discouraged by the repetitive ‘mismatches’ 
  • Don’t understand why they’re often told they’re being too picky or unreasonable
  • Claims to 'know their worth' and often view people they've met as 'settling'

Click for more

Passive Pesach

“I'm more the type to wait to be asked; not so much to take initiative.”

Passive Pesach

  • Relies on others to drive the relationship forward, avoids taking the initiative themself
  • Waits for others to make decisions
  • Is comfortable letting others take charge
  • Appears hesitant or disengaged, even when he cares
  • May unintentionally leave others carrying the responsibility
  • Typically acts as if someone else is going to make decisions or take initiative
  • Often doesn't notice what needs doing

Click for more

Misstep Mike

"I genuinely care and try my best—but I keep making mistakes that make me look careless or uncaring."

Misstep Mike

  • May forget important details, commitments, or plans.
  • Sometimes loses track of time despite intending to be punctual.
  • Could make impulsive or awkward comments that don't reflect their intentions.
  • Makes preventable mistakes despite wanting to improve.
  • Might come across as unreliable, even though they genuinely care.
  • Needs systems and reminders more than simply trying harder.

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Sensitive Suri

“I get hurt more easily than most other people.”

Sensitive Suri

  • Gets hurt by comments, tone, or small oversights that others might barely notice.
  • Experiences emotional slights with unusual intensity.
  • Often interprets neutral or ambiguous interactions as criticism, rejection, or disrespect.
  • Finds it difficult to move past hurt once emotionally activated.
  • Needs significant reassurance, yet reassurance doesn't always feel reassuring.
  • May mistake feeling hurt for evidence that the other person has done something seriously wrong.
  • May leave the person they're dating feeling as though they must walk on eggshells.

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Overbearing Ozer

“I'm just passionate. I don't mean to take over."

Overbearing Ozer

  • May have a strong personality that naturally fills the conversation
  • Leaves others feeling there wasn't enough space for them
  • Speaks with confidence and enthusiasm, sometimes overwhelming others
  • Often shares more than asks, or turns topic back to themself
  • May unintentionally dominate conversations
  • Frequently expresses strong opinions with certainty
  • Is often surprised when described as overbearing or self-centered

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Insecure Isaac

“I’m always worried I won’t be enough for the person I’m dating.”

Insecure Isaac

  • Frequently puts themselves down.
  • Struggles to accept compliments.
  • Adjusts opinions and preferences to match the other person.
  • Avoids disagreement out of fear of rejection.
  • Seeks reassurance but struggles to believe it.
  • Focuses more on being liked than on evaluating the relationship.
  • May hide parts of themselves in an effort to seem more acceptable.

Click for more

Worrier Willy

“I tend to be endlessly fearful that something could go wrong or will go wrong.”

Worrier Willy

  • Is endlessly concerned about bad outcomes
  • No reassurance lasts long or is ever enough
  • Expects negative outcomes
  • Fixates on issues between dates
  • Small issues become overblown
  • Too worried to enjoy the process
  • Often assumes something is wrong with shidduch

Click for more

Anxious Abigail

“I'm constantly feeling nervous, especially between dates, and usually can’t figure out why.”

Anxious Abigail

  • Finds dating overwhelming and emotionally draining
  • Experiences extreme stress leading up to or during dates
  • Often doesn’t enjoy the process, even when things go okay
  • Tends to mentally shut down

Click for more

Obsessive Odelia

“I go all-in emotionally very fast, and get attached before I actually know the other.”

Obsessive Odelia

  • Gets attached emotionally super quickly
  • Overshares personal details or deep feelings prematurely
  • Wants to be in constant contact
  • Worries a lot that relationship will end
  • Looks for relationship to progress fast
  • Heartbroken if shidduch ends—even if it was just a few dates

Click for more

Tongue-Tied Tony

“I just can’t seem to find the right words when I need them. Communication doesn’t come easy, especially feeling under pressure.”

Tongue-Tied Tony

  • Lack of verbal skills
  • Feels overwhelmed when putting thoughts into words
  • Long pauses, vague responses, or deflecting questions
  • Often quiet or minimal input to conversations
  • May seem emotionally distant, though they’re not
  • Worries about saying the wrong thing
  • Hesitates by which time opportunity passed
  • Typically feels stuck when it’s time to share something personal

Click for more

Commitment-phobic Connie

“Things seem to go well … until the relationship starts to get serious.”

Commitment-phobic Connie

  • Struggles when the relationship gets serious
  • Invents minimal justifications to end shidduch
  • Experiences panic and dread dread about moving toward
  • Is convinced something must be wrong
  • Almost never feels ready to get engaged
  • Pulls away even after weeks of positive dating

Click for more

Detached Dan

“I like her on paper… but I’m just not feeling it.”

Detached Dan

  • Struggles to feel an emotional connection, even after multiple dates
  • Feels close to family/friends, but not dates
  • Breaks off dates even without fault
  • Uncomfortable or awkward receiving affection
  • Often, unclear how emotional connection should feel 
  • Even when things go right, still feels little or no emotion

Click for more

Overthinking Ollie

“How can I be sure this is the right person for me?”

Overthinking Ollie

  • Persistent uncertainty regardless of how many dates
  • Relentless second-guessing and self-questioning
  • No evidence or reason is ever sufficient to settle an issue
  • Often looks to buy more time to avoid making decision
  • Would rather walk away over making a decision
  • Fear making the wrong choice more than missing a good relationship
  • Highly unlikely to trust their gut feeling

Click for more

Fixated Fernando

“Looks really matter to me—If only s/he were more attractive, this would be perfect. I wish I could get past this, but I just can’t.”

Fixated Fernando

  • Fixates on one surface aspect—appearance, income, height, etc.
  • Ends shidduchim quickly despite everything else going well
  • Attributes discomfort to the other's "not enough-ness"
  • Secretly hopes external qualities will override internal barriers
  • Hopes excitement will rescue them from own ambivalence
  • Finds commitment difficult, but doesn’t consciously connect the dots

Click for more

Ambivalent Avram

“I'd really like it to work, but something is holding me back. It’s not a no—it’s also not a yes either.”

Ambivalent Avram

  • Avoids emotional depth, keeps conversations superficial
  • Often has many short shidduchim that don’t progress
  • Often warm and charming—but at times indifferent and apathetic
  • May disappear for stretches or prioritize other interests
  • Often gives mixed signals: interested one day, distant the next
  • Small issues have an outsized impact of motivation level
  • Uses “not sure” as a shield to avoid vulnerability

Click for more

Perfectionist Pinchas

“If it’s not exactly right, it’s wrong. I just can’t settle for ‘okay. What if there’s someone better out there?”

Perfectionist Pinchas

  • The anxiety of “what if” consumes her dating process
  • Slightest imperfection could be a dealbreaker
  • Feels there’s always something off
  • Tormented by the prospect of someone better out there
  • Ends up scanning for flaws instead of looking for connection
  • Compromise feels more uncomfortable than being alone
  • Accepting anything less than perfection feels like “settling”
  • If there’s even a small imperfection, is convinced won’t be happy

Click for more

Fearful Feivel

"I’m not meeting people who make me feel comfortable."

Fearful Feivel

  • Frequently ends relationships, often after several dates
  • Focuses on what could go wrong, even when dates are going well
  • Is guarded about their emotions / reluctant to become vulnerable
  • Keeps searching for reasons not to move forward
  • Magnifies small concerns into major risks
  • Never feeling ready, always outstanding issues 
  • Highly likely to want to take breaks
  • Brings up issues later on that weren’t an issue before

Click for more

Disappointed Debbie

“Every time I think I found the one, something ruins it. I get excited at first—and then reality sets in.”

Disappointed Debbie

  • Gets  swept up in the potential — then crashes upon seeing a flaw
  • Holds a strong mental checklist of must-haves
  • Feels let down when dates don’t live up to unrealistic early impression
  • Intolerant of normal flaws or inconsistencies
  • Longs for a perfect alignment, and is crushed when reality hits
  • Often compares dates to an idealized vision of a spouse
  • Denies having elevated expectations
  • Likely blames failure on the other’s imperfections

Click for more

Infatuated Ita

“We just met, but I know we’re getting married. Perfect in every way. That's all I could think about.”

Infatuated Ita

  • Gets swept up in intense feelings of admiration and excitement early on
  • Sees the other person through a lens of idealization, focusing on their best qualities
  • Imagines a future together almost immediately, feeling as though everything clicks
  • Has scant interest in the facts and overlooks any red flags or doubts
  • Daydreams about the relationship constantly and struggles to function normally
  • Struggles to keep things in perspective, prioritizing excitement over realistic assessment
  • Tends to feel a sense of urgency to move things forward quickly

Click for more

Indecisive Izzy

“Dating would be great if I didn’t have to make any big decisions. They paralyze and terrify me. Like, what if I make the wrong choice?”

Indecisive Izzy

  • Struggles to move from “neutral” to a decision—even after many dates
  • Makes endless pros and cons lists but still feels stuck
  • Often consults multiple people, but only gets more confused
  • Hesitates to end it or move forward—worries about regret either way
  • Feels pressure to be 100% sure, fearing the weight of lifelong consequences
  • Secretly hopes the other party will end it, so can be put out of their misery
  • Will sometimes actively sabotage the relationship to avoid decision
  • Often feels relieved when shidduch ends, as they avoided a decision

Click for more

Evasive Esther

“I’d rather not get into all that right now… perhaps we can circle back to it later.”

Evasive Esther

  • Avoids deep or personal conversations, keeps things light and casual
  • Frequently redirects conversations away from emotional topics
  • Feels uncomfortable sharing personal details or thoughts
  • Feels anxious or exposed when discussions move toward meaningful connection
  • Worries that revealing too much could lead to judgment or misunderstandings
  • Prefers an easygoing, no-pressure dynamic, and avoids direct questions or serious talks
  • Chronically procrastinates when dealing with matters of a more personal nature

Click for more

Independent Itzik

“I’d get married if it was the right person, but I have a pretty good life being single. If things work out, fine. Otherwise, I'm good on my own.”

Independent Itzik

  • Values personal freedom and self-sufficiency, and is reluctant to surrender them 
  • Often think they don’t need a relationship to feel whole
  • Prioritizes personal goals and interests, and can even resent the need to date
  • If relationship makes too many demands will hold tightly to their independence
  • May push people away when they try to get too close or suggest a deeper connection
  • Struggles to open up emotionally, keeping things at a surface level
  • Is typically less willing to make concessions or adjustments to make it work for other

Click for more

Clueless Kalman

“I try my best and think dates go well, but I keep hearing I’m doing it wrong. Dating feels like a mystery.”

Clueless Kalman

  • May find conversations awkward or hard to keep flowing naturally
  • Dating etiquette is often confusing
  • Could have hard time planning and managing dates
  • Often can’t think of suitable topics for conversation or discussion
  • May struggle to ask meaningful questions or show genuine curiosity
  • Might unintentionally come across as distant or disinterested 
  • Sometimes misses simple social cues or emotional signals
  • May not use first name or not escalate the connection

Click for more

Complex Kayla

“There’s always something that feels off—no matter who I date. Part of me wants this… but another part is screaming no.”

Complex Kayla

  • Has two distinct sides to their character, such as introverted and extroverted
  • Find themselves drawn to very different types of people—none feel quite right
  • Feels pulled in opposing directions, often without fully realizing why
  • May idealize a “perfect fit” who could somehow satisfy both sides of their personality
  • Can appear picky or hard to please, but it’s really an internal tug-of-war
  • Due to low satisfaction is typically certain that their dates aren’t “the one”
  • Often has an extensive history of shorter dating experiences

Click for more

Conflicted Casey

“No matter what I pick, it feels like I’m leaving something important behind. I wonder if I know what I really want.”

Conflicted Casey

  • Whomever they date, they feel that they aren’t being true to a part of themselves
  • Struggles to feel satisfied because of some negative feeling, such as shame or guilt
  • Can be drawn to someone, then feel restless later 
  • Often wants to make a decision, but is left second-guessing with a pit in their stomach
  • Often a struggle between what they think would make them happy versus what they feel is right
  • Often manifests as conflict between what they prefer versus what they were taught or raised to value
  • May flip-flop on what they're looking for, depending on who they're speaking to
  • Often wishes someone else could just tell them what to do

Click for more

Naysayer Noam

"There’s no way that’s for me. It was clear from the first second. What were they even thinking?"

Naysayer Noam

  • Has a tendency to write people off quickly, assuming they're not a good match
  • Feels like every date is with someone who doesn’t fit their ideal or values
  • Often think they’re being misunderstood, frustrated at shadchanim  
  • Gives a hard no, is rarely open to another point of view
  • Feel they’re wasting their time, get discouraged by the repetitive ‘mismatches’ 
  • Don’t understand why they’re often told they’re being too picky or unreasonable
  • Claims to 'know their worth' and often view people they've met as 'settling'

Click for more

Passive Pesach

“I'm more the type to wait to be asked; not so much to take initiative.”

Passive Pesach

  • Relies on others to drive the relationship forward, avoids taking the initiative themself
  • Waits for others to make decisions
  • Is comfortable letting others take charge
  • Appears hesitant or disengaged, even when he cares
  • May unintentionally leave others carrying the responsibility
  • Typically acts as if someone else is going to make decisions or take initiative
  • Often doesn't notice what needs doing

Click for more

Misstep Mike

"I genuinely care and try my best—but I keep making mistakes that make me look careless or uncaring."

Misstep Mike

  • May forget important details, commitments, or plans.
  • Sometimes loses track of time despite intending to be punctual.
  • Could make impulsive or awkward comments that don't reflect their intentions.
  • Makes preventable mistakes despite wanting to improve.
  • Might come across as unreliable, even though they genuinely care.
  • Needs systems and reminders more than simply trying harder.

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Sensitive Suri

“I get hurt more easily than most other people.”

Sensitive Suri

  • Gets hurt by comments, tone, or small oversights that others might barely notice.
  • Experiences emotional slights with unusual intensity.
  • Often interprets neutral or ambiguous interactions as criticism, rejection, or disrespect.
  • Finds it difficult to move past hurt once emotionally activated.
  • Needs significant reassurance, yet reassurance doesn't always feel reassuring.
  • May mistake feeling hurt for evidence that the other person has done something seriously wrong.
  • May leave the person they're dating feeling as though they must walk on eggshells.

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Overbearing Ozer

“I'm just passionate. I don't mean to take over."

Overbearing Ozer

  • May have a strong personality that naturally fills the conversation
  • Leaves others feeling there wasn't enough space for them
  • Speaks with confidence and enthusiasm, sometimes overwhelming others
  • Often shares more than asks, or turns topic back to themself
  • May unintentionally dominate conversations
  • Frequently expresses strong opinions with certainty
  • Is often surprised when described as overbearing or self-centered

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Insecure Isaac

“I’m always worried I won’t be enough for the person I’m dating.”

Insecure Isaac

  • Frequently puts themselves down.
  • Struggles to accept compliments.
  • Adjusts opinions and preferences to match the other person.
  • Avoids disagreement out of fear of rejection.
  • Seeks reassurance but struggles to believe it.
  • Focuses more on being liked than on evaluating the relationship.
  • May hide parts of themselves in an effort to seem more acceptable.

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