How to Date Someone Who’s Out of Your League

Hey, did your phone just ding? It sounded like a match. Congrats! But oh, what’s this? The match is someone super hot you swiped right on with the assumption they’d never actually swipe right back?

It’s all fun and games when you’re maniacally swiping late at night, approving every cool-looking person who appears on the screen, but it gets more serious when you remember they’re real people who can — and just might — like you back. It’s a blessing and a curse to go out with someone who is drop-dead gorgeous or has an ultra-cool job. On the one hand, it’s a dream come true…but on the other, it can be a mortifying reminder of your own insecurities. Here’s how to get ready for a date with someone you think is out of your league.

Know how to hype yourself up

The key here is that you need to remember that they swiped right or agreed to go on this date because they saw something worthwhile in you. That alone should have you feeling great, no matter what it is about this other person that is making you so nervous.

“If someone agreed to the date and they’re not ghosting you, they most likely don’t think there’s a ‘league’ issue,” said Hannah May, a 26-year-old Chicagoan who describes herself as a lifestyle blogger and amateur dater.

“Remember that you have a lot to offer,” she said. “You need to focus on yourself and work on yourself before dating, period, or you’re not going to get anything out of it.”

Type out a list of all the cool, wonderful things about you. Ask a few trusted friends to contribute to what we’re sure is an already-lengthy list of your terrific attributes. Read that list. Internalize it. You’re fun! You’re attractive! The out-of-your-leaguer thought so when they agreed to meet up, so ask yourself why you’re experiencing self-doubt.

If the nasty internal monologue is the result of, say, put-downs from an ex, remember that those insults came from a place of hurt or maybe even projection, likely at a rough time as the relationship was disintegrating. Don’t let the negative, warped opinion of someone whose association with you was negative impact the way you see and project yourself going forward. You’re a lot cooler than you think you are, and you deserve to date someone awesome.

Role play from a better perspective

What would you tell a friend in this situation? Imagine that a beloved, lifelong pal came to you and said they were nervous for a date with someone hotter or more established than they are. You’d bug out, right? You’d — gently — tear them to bits for being so hard on themselves.

We all have people who love us, from family members to friends. Think about how hurt your mum or brother would be to hear you negatively comparing yourself to someone else. When you do this, you’re implying your own friends and loved ones have bad taste, you know. And they don’t!

Suggest meeting in neutral ground

If this person is a big-shot in the movie industry, don’t go to a Hollywood hot spot. If they’re a publishing powerhouse, don’t go to the bookstore. If you feel they have a slammin’ body, avoid the beach. Essentially, don’t go somewhere that is going to exacerbate the feelings of inadequacy you’re already experiencing and give them a leg up, even if they don’t realise you’re perceiving them to have the edge on you here. Instead, suggest a date location that is more neutral and doesn’t lend itself as a highlight to whatever you see as the incredible attribute in them that is making you so nervous.

Try to be reasonable

Have you ever seen the cover of a tabloid? If you have — and we know you have — then you know that even the hottest, most accomplished people in the world go through breakups. Ask yourself why that might be. Is it possible that being attractive or talented isn’t the only thing that matters in a relationship?

You already know that looks, awards, accolades, and clout get people far, but in order for anyone to have fulfilling relationships, they have to have substance, too.

Consider this: There is more to the person you’re about to meet up with than their angelic bone structure or high-paying job. Moreover, whatever else there is to them might actually suck. To put it plainly, you might not like them. If they were as perfect as you’re envisioning them to be, would they not already be securely snatched up by some equally-fancy person?

May pointed to advice that her cousin gave her: “Instead of worrying about if they like you, worry about if you like them. This mindset shift also helps with any jitters or anxiety.”

Don’t overcorrect here and go into the date thinking they’re damaged goods or anything, but be reasonable. A hot bod does not a perfect mate make.

Recognise your insecurity without taking it out on the other person

Look, you’re feeling nervous and insecure. That’s fine; it happens to everyone. But don’t take out your feeling of inadequacy on this person, who is probably perfectly nice and normal and likely has no idea you think they occupy some unreachable level of greatness. As we’ve established, they agreed to hang out with you for a reason. They think you’re interesting and attractive. This is almost certainly not a romcom-style joke where they’re going on a pity date with you, but even if it were, that would only be further proof they suck and are not the one for you.

“I’ve wasted so much time in my life overthinking texts and what to say and I feel like those situations never work out,” said May, who advises against worrying so damn much. “If someone’s for you, you won’t have to overthink your interactions or be left feeling confused.”

Don’t go into this defensively or expecting the worst. Give yourself a stern talking-to, go on the date, figure out if you have anything in common, and go from there like you would with anyone else. Whatever hangups you have are totally your own; this person has no idea that you don’t think you’re good-looking or you feel like you’re not advancing in your career. They just want to learn about you, so let them. Allow them and yourself to be surprised.