Inviting someone to join you on a date can be nerve-racking but with this simple advice you can be authentic – and hopefully successful.
If you’re single and hoping to find a romantic partner, you may be wondering how to ask someone out on a date. If you find the prospect daunting, fear not. We have consulted certified relationship and boundaries coach Rachel Rose, who can help you feel more confident when asking someone out. Who knows where that simple invitation could lead?
In this article
- Preparing to ask someone out
- Reaching out to your crush
- Planning the date
- Asking someone out over text
1. Build confidence
If you haven’t been on the dating scene for a while, putting yourself out there may feel strange. But building your confidence can be easier than you think with a simple switch of mindset. “Half the nerves come from this mental ‘what if’ spiral where you imagine every worst-case scenario,” says Rachel. “Our brains just love to mess with us. Instead, think of it as just two people hanging out. Shift your mindset to ‘I’m curious about this person’ with no pressure to label them as The One.” Just remember, this isn’t a lifetime commitment – simply a way of getting to know someone new.
2. Plan your approach
No one wants to be that person that starts asking all and sundry out on a date. Those who are newly single can be prone to this. So think carefully about how you’d like to approach the dating scene. There may be someone you already know that you’d love to get to know better, or perhaps you’ve found a potential match on a dating site that you’d like to meet in person. But how do you pluck up the courage to ask them out?
“Build-up is everything,” says Rachel. “Start with humour. Make them laugh a few times via text or in person to create a little emotional connection.” Making someone laugh actually eases tension and starts building trust. It also helps lower any feelings of discomfort. “Asking someone out can feel a little intense, so bringing a light-hearted tone makes the whole thing less intimidating. Keep it warm and casual, and they are likely to be more open to a yes.”
3. Choose the right moment
Finding the right moment is integral to setting things off well with a potential love interest. For instance, if you’re asking them in person, look out for positive body language such as their eyes lighting up, smiling, or playing with their hair or clothes. “If you’re texting, notice if they start referencing things like ‘when we hang out’ or using flirty emojis,” Rachel says. These cues will let you know when the feeling is mutual and it’s the right moment to ask for a date.
- Learn more: What signs show someone likes you romantically?
4. Introduce yourself (if you haven’t already)
Asking someone out that you don’t know but have admired from afar can seem intimidating, but Rachel says the key is in finding a purpose. So think about how you can start a conversation with them first. “If they’re lifting weights, maybe ask about a workout tip.” Likewise, if you see them on your daily dog walk, maybe ask them a question about their pet or the local area.
This, says Rachel, is a good way to gauge if they’re interested. “Most importantly, don’t assume just because you’re into them that they’ll automatically feel the same. Approach respectfully, then if they seem into it, suggest sharing something useful (like a relevant link or group). Then ask for their details to send it along, letting things naturally flow from there.”
Things to consider when asking your crush out
5. Be direct and clear
While dating in your twenties may have meant playing mind games and pretending you didn’t want commitment, dating as a mature adult can be more straightforward. Yes, it may be too much to say you’re looking for marriage on the first date, but if things are going well after the second or third date, it’s fine to be direct and clear about what you’re looking for in a partner.
“Use what I call ‘transparent advertising’,” says Rachel. “If marriage or something long-term is on your mind, say it outright but at the right time. Avoid the whole playing-it-cool act as nobody benefits from it.” Authenticity is integral to avoiding a potential mismatch with someone who wants different things.
6. Suggest a fun activity
Choosing what to do on a first date can be anxiety-inducing but planning a fun activity can help to break the ice. Whether you go to a bowling alley, salsa class or sip-and-paint evening, there will be plenty of other people and activities to spark conversation and fun. It will also show initiative on your part and reveal your adventurous side.
7. Be yourself
We all want to make a good first impression but even if you’re trying to start afresh, it’s important always to be yourself. “Here’s the truth,” says Rachel. “Nobody can keep up a fake personality forever. Psychologically, it’s just not possible to play a role for more than three to six months before our true selves slip out.
Sure, pretending could attract people you normally wouldn’t, but when the real you surfaces it can break the trust,” she says. “And constantly adjusting who you are for someone else’s approval is what I call ‘micro self-abandonment’.
8. Understand what a subtle or disguised “no” is
If the other person is afraid of hurting your feelings and doesn’t know how to say no, they may avoid a clear refusal when you ask them out. In this case, you should watch out for signs of a disguised “no, thank you”.
“If someone’s being inconsistent or evasive, it’s often a way of saying ‘no’ without being direct,” says Rachel. “It usually comes from people who are conflict-avoidant, assuming disagreement leads to a fight.” If you’re unsure, Rachel suggests just asking a direct question. Everyone deserves to know where they stand.
How to ask someone out over text
Keep it light
Texting is part and parcel of modern life but when it comes to asking someone out, there’s still a certain etiquette. First, keep things polite and light and avoid writing essay-length messages. Rachel suggests talking in a playful way about something you’d like to do together, such as, “We should check out that new Italian restaurant in Mayfair – what do you think?”
Give them time and space to respond
While you may be keen for a response as soon as possible, don’t follow up with another text before your recipient has had time to answer. Even if you can see those tell-tell blue ticks telling you they’ve read the message, be patient. People have busy lives and other commitments, so a delayed response doesn’t mean they’re going to say no.
Entering the world of dating can feel challenging but it should also be fun. So try to forget any long-term plans for now and concentrate on enjoying getting to know someone new. Build up your confidence, plan your approach, and think of something fun to do together. The rest will happen naturally.
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FAQs
How long should you wait to ask someone out?
While you shouldn’t rush into asking someone out, you don’t want to wait so long that you become friends or drift apart. Beyond that, there is no strict schedule to follow. If you have met online, you may have exchanged a few messages that suggest a growing rapport between you. Now is the time to ask them out on a date. If you first met in person, allow the conversation to flow and watch for signs of mutual attraction before you consider asking them out.
What should I say when asking someone out?
Keep the tone light-hearted. A touch of humour can work wonders. After all, if you seem fun and friendly when you ask someone out, they will feel more inclined to spend time with you. Go for a casual approach so the other person feels no pressure. A first date is simply a chance to get to know each other a bit better.
What to say if someone rejects you?
Of course, by asking someone out you run the risk of rejection. This can be painful but as the saying goes: nothing ventured, nothing gained. Ultimately, the way you accept a “no” to a date should be just as gracious as the way you accept a “yes”. Sure, it may be a little embarrassing but it’s important to be courteous and take it on the chin.