I don't know how to ask people out on a date

Thursday | August 8, 2024

Love Letters Dating

I don’t know how to ask people out on a date

Hi LL,

How old is too old to learn how to ask people out and to learn how to date? I am an introverted guy rapidly approaching his 40s, has very little relationship experience – none initiated by me – but I am very lonely and would like to be in some sort of dating relationship. Is it too late for me to learn those basic social skills?

Side question, given my lack of experience, would it even be ethical to put women through the very unnerving, day-ruining experience of me and my social anxiety asking them out? The idea of gaining self-confidence at the expense of someone else does not sit too well with me.

What do you think?

Thank you for your time,

– Letter Writer

p.s. Yes, I am in therapy for my anxiety.

p.p.s I have tried dating apps on and off for years, definitely not a good fit.

Yes, it is ethical to ask people out – assuming you’re interested in them!

Why would you see the process as gaining self-confidence at someone else’s expense? A lot of people love getting asked out, even if they wind up saying no. It’s a flattering thing! It can be very nice, especially when the asker makes it clear that there’s no pressure.

Please know that dating apps have made people so practiced at asking people out (via message) that they might be too good at it. There’s not much thought sometimes, and there are a lot of people who’ve had a zillion first dates but no time for self-reflection.

At your age, there are also a ton of people getting out of monogamous relationships of many years. They know how to court and relate to one person. Now they’re in your boat, wondering if they have the skills to initiate something different in 2024.

I’ll admit I’m very tempted to get you on Zoom with some friends and have you ask us out a few times for practice. Because while these pals and I are not available, perhaps, we are in our 30s and 40s and have been approached many ways … and we have approached others … and sometimes it’s nice to be in a safe place and throw spaghetti at a wall and see what sticks for people.

Anyway, we can discuss. Maybe it’d make a good podcast episode.

In the meantime, know you’re OK. Know that lots of people are lonely and dealing with social anxiety. Believe that someone is waiting to be asked out – and would be thrilled to hear from you.

– Meredith

Readers? Is it an inconvenience to be asked out? Any tips on trying this? What’s your line when you ask someone out?

What’s been on your mind about your dating/relationship life? Ask your own question. It helps others who are wondering the same thing. Use the anonymous form or email [email protected].

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Featured Comment

Think of how you’ve made friends growing up and it’s a similar thing. Are there groups you could join that focus on interests or hobbies? Not even necessarily to meet women, just to meet people and to get in the habit of interacting. It’ll take some of the pressure off and you’ll have fun, too. Just don’t overthink it! Remember that most people are unsure of themselves out there.

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