How to Start Dating Your Crush

Last Updated: January 8, 2023

When the crushing ends and the other person on the receiving end finally agrees to an actual date, you need to shift from fantasy to reality. A date is a real thing, and the person you're dating, is a real person. All the things you've been fantasizing about may not come to be when dating, so you'll need to keep things realistic and sensible.

Steps

1
Dress well. Stay within your usual style but ensure that it's neat, clean and fresh-smelling. Even go so far as to iron your clothes, it's a novelty not much attended to anymore but screams stylish and attentive to the small details. It'll be a great way to impress your crush-turned-date.^{[1]
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- Ensure that your hair is neat or casually styled messy.
- Don't overdo the clothing. This person has said yes to dating you because they already likes the way you're presenting yourself.
2
Stop viewing this person as your crush. Now that they are a date, start using this term instead. This helps you to accept the transition from dreaming about the person to actually spending time with them.^{[2]
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Expert Source

Christina Jay, NLP
Dating & Relationship Coach
Expert Interview. 11 February 2020.} Watch out if you don't make this transition, as you could be setting the poor person up for a fall when they don't live up to your expectations born of dreaming.

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3
Be enthusiastic, pleasant and confident. Tell yourself the date is going to go well and act in this fashion.^{[3]
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Research source} You've been crushing over this person for ages, now it's time to actually get to know them, so see this as a great opportunity, not a scare-fest.^{[4]
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Expert Source

Christina Jay, NLP
Dating & Relationship Coach
Expert Interview. 11 February 2020.}
4
Be positive from the outset. Always speak positively about people you know that they can relate to. This reveals that you're no gossip and that you're a supportive kind of person. And aim to keep the conversation as positive as possible. You and your date can carry on together with positive comments, while negative things are usually a conversation stopper.^{[5]
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- Crack some jokes if you're comfortable doing so. Ensure that they're genuinely funny and avoid any jokes that require the debasing of others.
- Be self-deprecating. You could even mention some funny facts about how things were for you when you were crushing on your date and how great it is now that you're actually dating.
5
Let your date talk about themselves more than you talk about yourself. This gives them power to speak comfortably and freely about themselves which they will enjoy. Ask plenty of questions to encourage your date to talk and tell more about themselves. This is both polite and an important part of replacing your mysterious fantasies with the actual facts.^{[6]
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6
Be thoughtful and considerate. Offer a drink or bite to eat. This will show that you care about them. Be certain to ask in a sincere way.
7
Tell your date what a wonderful date you've had together. Lead up to asking for a second date, or for hanging around together a whole lot more. If things have gone well, your date will likely say yes.^{[7]
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Expert Q&A

Question

How can I win over my crush?

Christina Jay, NLP
Matchmaker & Certified Life Coach
Christina Jay is a Matchmaker and Certified Life Coach based in Toronto, Ontario, Canada. Christina is the founder of Preferred Match (preferredmatch.ca), her matchmaking service that finds love for successful and elite individuals. She has over 10 years of coaching experience, earned her NLP (Neuro-linguistic Programming) certification through NLP Canada Training, and has a BA in Business Administration from Brock University.

Christina Jay, NLP

Matchmaker & Certified Life Coach

Expert Answer

I would say, just be yourself. Try to remain calm, open, and honest. They may like you just as much as you like them, so try not to overthink it.
Question

How can I get closer to my crush?

Christina Jay, NLP
Matchmaker & Certified Life Coach
Christina Jay is a Matchmaker and Certified Life Coach based in Toronto, Ontario, Canada. Christina is the founder of Preferred Match (preferredmatch.ca), her matchmaking service that finds love for successful and elite individuals. She has over 10 years of coaching experience, earned her NLP (Neuro-linguistic Programming) certification through NLP Canada Training, and has a BA in Business Administration from Brock University.

Christina Jay, NLP

Matchmaker & Certified Life Coach

Expert Answer

I would try asking them out on a date. Ask them if they would like to grab a bite to eat with you. Avoid going out with a group of friends, and invite them to go out one-on-one. If it's just the two of you, it may turn into something more.
Question

How do you talk to your crush?

Christina Jay, NLP
Matchmaker & Certified Life Coach
Christina Jay is a Matchmaker and Certified Life Coach based in Toronto, Ontario, Canada. Christina is the founder of Preferred Match (preferredmatch.ca), her matchmaking service that finds love for successful and elite individuals. She has over 10 years of coaching experience, earned her NLP (Neuro-linguistic Programming) certification through NLP Canada Training, and has a BA in Business Administration from Brock University.

Christina Jay, NLP

Matchmaker & Certified Life Coach

Expert Answer

Try to be open and flirtatious. Give them subtle hints that you like them, such as giving them compliments here and there. That can be more than enough for them to know that you're interested in them.