A Single Guy’s Grades Of The 10 Worst First Date Ideas

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As a veteran of the Bumble / Tinder / Hinge dating era, I have been on a lot of first dates. Some went exceptionally well, some were unmitigated disasters, but most were fairly unremarkable. Almost all have followed the same basic blueprint: happy hour drinks on a weeknight. It’s light, not a lot of pressure, but with the option to extend the night further along if things are going really well. And if it is, the second date on a weekend evening is very easy to set up in advance. Granted, it’s not incredibly original, but the drinks date is a reliable go-to.

Apparently, however, some of my companions are taking some ill-advised risks with regards to first date ideas. Now, I’m not one to judge others who want to be creative for a potential paramour, but there is a line between creative and foolhardy. According to a survey of matchmakers, these are the ten worst ideas for a first date one can come up with. Ever the contrarian, I will attempt to make the case for each of these, giving the poor souls who thought them up the benefit of the doubt.

To be clear, I would never do a first date at any of these places or events, nor would I advise any of you good people to do so. Nevertheless, I’ll give it my best shot to make them workable for you if need be.

1. Fast-Casual Restaurants (e.g. Chipotle)

Honestly, this is the easiest one to justify. If you or your date aren’t drinkers of either alcohol or coffee, a quick bite at a fast-casual joint brings the same relaxed air. There’s no deep commitment to a long, drawn-out meal, so you can dip out whenever you feel the date going sour. Everyone’s eaten at one of them, and everyone has their favorites, which makes it relatively easy to find an option that works for both of you.

In addition, this might be the best option available if you want to have a lunch date. These places are usually among the few restaurants that will be convenient for both of you to get in a meal and get back to the office within an hour.

Is it incredibly romantic? Not at all. But it’s low-pressure and innocuous enough that it will still accomplish what a first date is meant to: make sure the other person isn’t crazy and/or incredibly incompatible.

Grade: B+

2. Netflix and Chill

You ever matched with someone, and within the first few messages you know it doesn’t have legs? We’ve all been there, texting with someone who just doesn’t get you excited. You’re not checking your read notifications to see if they’ve responded yet, or carefully reviewing the flow of the conversation to judge how long you have to wait before responding. They’re just another face with the sort of genitalia you fancy, nothing more or less.

For this type of superficial, casual date, I’m 100% down with the “Netflix and Chill” option. Is it lazy, sleazy, and cravenly obvious about your intentions? For sure, but you’re not throwing this option out to someone you really want to impress. This is the Tinder age, folks. We’re adults. When you know the score, and the relationship ceiling with this person is FWB, shoot your shot.

If you do actually see some possibility of liking the other person and wanting to date them, yeah, this is probably not the impression of a first date you want to give.

Grade: A+ / D- (for actual relationships)

3. A Local Bar Where You’re a Regular

This is the first one on the list that makes me feel personally attacked, okay? These matchmakers who made the list say that you don’t want to seem like an alcoholic, or have your past drunken shenanigans make a bad first impression. But going somewhere where “everyone knows your name” is a great way to show that you’re not an anti-social shut-in. In all likelihood, if you’re a regular you’re friends with the bar staff who can talk you up to your date. It’s also a great judge of compatibility; if your date doesn’t like your favorite bar, that does not bode well for the longevity of a possible relationship.

This is like giving up home-field advantage because you don’t want the opposing team to get rattled by the crowd. Rookie move.

Grade: A+

4. A Family Gathering

For a blind first date, yeah this is a tough one to justify. But, if you’re dating someone who knows your family – the friend of a sibling, a family friend, etc. – a family gathering can be a fun, relaxing “semi-date” to gauge your compatibility. If your family is generally awesome, like mine, your date isn’t going to be getting grilled by Aunt Deborah about when she wants to have kids. She’ll be hearing endearing, yet slightly embarrassing, stories about your childhood.

If you could see your date getting invited and attending a gathering like this before you mustered up the courage to ask them out, green light in my book. That said, this is a very pressure-packed situation, especially if you have some overbearing and/or creepy relatives in attendance. If they aren’t enthused about possibly having your first kiss in front of Uncle Ted, back down.

Grade: C

5. A Soulcycle Class

This is really only applicable to those people who brag about wanting a “swolemate” on their Bumble profiles (side note: please stop, it’s gotten to the level of obnoxious that using “Tinderella” reached last year). These are the people who would invite a first date to a spin class. Or rock climbing. Or a gym session. If being in shape is that important to you and you want to meet someone who will be doing couple activities like this, go ahead and throw this out there. But if you run into a NARP like myself who would rather do almost anything other than exercise in front of someone he wants to impress, it’s a no go.

Oh, but please do not try to use this as an opportunity to double-dip, and just take a guy to your regularly scheduled Thursday night class because you’re too lazy to set aside time for a real date. This applies to almost all non-recreational opportunities. Actually make a date about the other person, not shoehorning it into whatever you were going to do anyway.

Grade: B-

6. Your Birthday Dinner

See the above points for family gathering; this has to be someone you would have invited regardless. If not, please do not make a stranger have to go through the pressure of wondering if they need to get someone they’ve texted less than 20 times a gift. There’s even more pressure in this instance than a family gathering since this event is all about you. Presumably, you’re going to be talking to a lot of friends and family throughout the night. You won’t have the same opportunities to excuse yourself for a little bit and have an intimate conversation. This leaves your date to be forced to make small talk with people whose only common connection is knowing you.

As an aside, I was once invited to go to someone else’s birthday (whom I did not know) on a first date. It was awkward AF (more awkward than a first date or birthday with me would normally be). Same rules go: don’t force strangers into an intimate setting where they don’t know anyone.

Grade: D

7. A Wedding

Unless they themselves were invited to the wedding independent of you, this is an absolute non-starter. Even then, a first date before the actual wedding would be advisable, just to test the waters and avoid any drama at the actual wedding. This is about the bride and groom’s love story, not about you trying to start your own. Save your indiscriminate macking for the drunken, sad bridesmaids.

Grade: F

8. Out with a Group of Friends

This is much easier to pull off than family gathering or birthday dinner. Yes, you still are breaking the principle of having a stranger in a position of not knowing anyone, but there is a lot more wiggle room. Maybe your date knows some of the friends you’ll be out with. You might have a group large enough that you’ll be able to break off and devote quality time to him or her. Even better, it might be during some activity he or she is very enthused about.

In a scenario where your friend group and hers are overlapping, and you’ll be able to be alone having fun, this is a fine option for a first date. You’ll be relaxed, and each will have an outlet to relieve some pressure and have space if things get weird. It will also subtly create an image of how your life as a couple could be, doing activities with people you love. This is a judgment call that comes down to how comfortable you both will be with the group, how much fun the activity is, and how much time you’ll spend together. But in ideal circumstances, this is a good idea.

Grade: A-

9. Disneyland or an Exorbitant Vacation

Unless you are a member of the royal family, the Trumps, the Gates, the Zuckerbergs, or some other billionaire dynasty family, and you’re trying to impress someone with similar status, I don’t know who in their right mind would think this is okay. There’s trying too hard, then there’s trying like a Herculean effort too far. Even if you are mega-rich, this move just screams “I have nothing in my life, looks, or personality to impress you, and I have no understanding of societal norms!”

First dates work best when they’re in a relaxed, low-key environment where you can get to know the other person and judge whether or not you’d like to have them exist in your world for more than an hour. A weekend away in Napa is basically the Saw version of a first date. Don’t make a girl have to chop her arm off because she realized you’re way too into Crossfit about two hours after meeting you.

Grade: F

10. A Noisy Dance Club

This is not where you take the first date. This is where you find someone with whom you can bypass the first date and skip right onto that “Netflix and Chill” (ugh) date mentioned before. Unless both of you are cool with a relationship that will be primarily focused around EDM concerts, dropping Molly, and way too many strobe lights, reconsider.

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