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Should I date him or not?

Dating can be complicated. When you meet someone new, it’s hard to know right away if they are a good match for you. There’s a lot to consider when deciding if you should date someone. Ultimately, only you can make the right choice for yourself. But asking some key questions can help provide clarity.

How do I feel when I’m with him?

Pay attention to how you feel when you spend time together. Do you feel happy, comfortable, and at ease? Or are you tense, bored, or annoyed? Your emotions are telling. If being together feels effortless and fun, that’s a good sign. But if you feel like you have to work too hard to have a good time, he may not be the best match.

Do we have chemistry?

Chemistry is important in a romantic relationship. You want to feel attracted to him and excited to be close. This doesn’t have to mean instant fireworks. But you should feel drawn to him in some way. Think about your physical and emotional connection. Do you feel electricity when you kiss or hold hands? Do you find it easy to open up to him? Strong chemistry indicates potential for a deeper bond.

Are our values aligned?

Having shared values and life goals can strengthen a relationship. Consider your views on important things like family, career, morals, and goals. Do you seem to want the same things out of life? Are your worldviews relatively compatible? You don’t have to agree on everything. But having some core things in common makes it easier to build a life together.

Do we have fun together?

A good sign is when you genuinely enjoy each other’s company. You like doing everyday things together, big and small. Even quiet nights at home feel fun with the right person. And your differences can bring you closer too. A healthy relationship includes laughter, adventure, intellectual stimulation, and lighthearted moments.

How does he treat me?

Pay close attention to how he behaves towards you. A caring partner will be respectful, trustworthy, supportive, and affectionate. You should never feel belittled, controlled, or unsafe. He should value your opinions and needs. Small things like listening attentively, being reliable, and making you feel special go a long way. But beware of extreme flattery or “love bombing” early on as potential red flags.

How does he handle conflict?

Fights and disagreements are inevitable, even in healthy relationships. What matters most is how you resolve conflict together. A good partner stays calm, communicates clearly, compromises when needed, and treats you with kindness even when upset. Beware if he gets aggressive, defensive, avoids difficult conversations, or acts cruel or passive-aggressive during arguments.

Am I being my true self?

You should feel comfortable being yourself with someone you’re dating. That means you can share your real thoughts, feelings, interests, and needs. If you find yourself hiding parts of your personality, that’s a red flag. You want someone who appreciates you for who you are. And you should feel free to change and grow without judgment.

Is this moving at a comfortable pace?

Rushing into a romantic relationship can be risky. Be wary if he pushes for serious commitment too quickly. Moving slowly allows you to get to know each other at a more genuine level. You’ll also have time to assess compatibility without attachment or pressure clouding your view. Proceed thoughtfully, tune into your instincts, and don’t ignore warning signs just because he seems perfect in the beginning.

Do I trust him?

Building trust is vital for a strong foundation. Really listen to your gut feeling about his trustworthiness and integrity. Small lies, broken promises, and secrecy are big red flags. But also notice if he keeps his word, respects your privacy, and is honest with you even about hard things. Trust develops slowly over time. If you find yourself questioning it early on, that’s very telling.

Am I compromising my boundaries?

Healthy relationships allow both people to maintain their own boundaries. You shouldn’t feel like you have to say yes to everything to keep him happy. Nor should you ignore uncomfortable situations or go against your core values. Look for instances where you may be rationalizing or making excuses for bad behavior. Sticking to your standards will help you make the right choice.

Can I be vulnerable with him?

Emotional intimacy is important for a relationship to deepen. You should feel safe opening up to him about your insecurities, fears, and dreams. Can you express your feelings without judgment? Do you help each other through tough times? Intimacy means you’ve seen the best and worst in each other, and chosen to stay. If either of you seem closed off, that’s something to address.

Is this relationship emotionally healthy?

Healthy dating relationships make you feel secure, supported, and respected. You support each other’s growth as individuals. There’s space for open communication, quality time together and apart, trust, and affection. You resolve conflicts fairly and make compromises. And you both feel excited about the relationship most of the time. Don’t ignore emotional abuse such as controlling behaviors, jealousy, manipulation, criticism, or isolation. These are toxic signs.

Do I like who I am with him?

Some people bring out the best in us, while others don’t. How do you feel about yourself in this relationship? More confident, motivated, and happy? Or insecure, stressed, and drained? The right partner will make you feel valued for who you are. And you’ll find yourself becoming a better version of yourself. If the relationship seems to diminish your self-esteem, that’s a major warning sign not to overlook.

Pros and Cons List

Creating a simple pros and cons list can provide clarity when you’re on the fence about dating someone. Here’s an example:

Pros Cons
Funny and intelligent Messy and disorganized
Adventurous and spontaneous Immature with money
Supportive of my career Different political views
Great chemistry physically Very close with his ex

Looking at the major positives and negatives side-by-side makes it easier to weigh them objectively. Think about which pros and cons would be deal-breakers or must-haves for you. Trust your judgment.

Is the timing right?

Even if you have chemistry, similar values, and strong communication, the timing still needs to be right. Consider what’s going on in each of your lives. Are either of you getting over a breakup, starting a new job, moving, or making other big transitions? While dating can enrich your life, it also requires time and energy. Make sure you’re ready to balance a new relationship with individual responsibilities. Don’t let infatuation rush you into dating prematurely.

Do friends and family like him?

Get some outside perspective from people you trust. What do your friends and family think about him? Do they see red flags you might have missed? Are they voicing reasonable concerns? Or do they see your chemistry and rapport? Loved ones often notice things you can’t see when caught up in romance. Value their support and guidance, even if you don’t always agree.


Dating is complicated, with many factors to weigh. Focus on listening to your instincts and evaluating the relationship thoughtfully. Don’t ignore any warning signs or rationalize bad behaviors. Be true to yourself and what you want in a partner. Making a wise, informed decision now can lead to long-term relationship happiness. Trust your heart, mind, and the advice of loved ones. If he’s the right match for you, it will feel clear. And if he’s not, have faith you’ll find the kind of love you deserve.