I’ve been on tons of dates—both great and utterly disastrous. By far the best ones I’ve ever had shared common threads: they were about us and only us. There weren’t distractions or “Oh boy…” moments brought upon by third parties or outside forces.
It’s easier than you think to have a fully connected date. In fact there are 5 particular things you can do to better it on all ends:
Care more about him more than the drinks.
I don’t care if we go to a place with drinks, i.e. any restaurant ever, or a bar. It’s a public place with a purpose of being social. That’s the ambiance and it’s great, but alcohol plays a heavy hand in it too. Try not to drink because you think he’ll think it’s funny or to try and get you comfortable.
One thing I like to do is never order a drink unless he’s drinking as well. If you arrive early, don’t order a drink because Lord knows you’ll be hammered by the time he gets there. If he sips slowly, so shall you. That solves everything. The reason why you’re there isn’t to get hammered, but to be here with him. Together.
Choose places that bring out the best in both of you.
If you happen to know he’s uncomfortable in large group settings, don’t purposely plan on taking him to a crowded club—that’s stupid, right? Think of the atmosphere: you want it to bring him closer, not separate him completely. It’s not hard.
Remember there is beauty in simplicity. Go for a walk, enjoy an outdoor brunch, go to the farmer’s market and shop for groceries, play with puppies at the dog park. Don’t be fooled either. Sometimes a great idea might have a hidden problem, for example: taking him to the theatre is a good idea, but not if the subject matter is something he’s deeply uncomfortable with (you don’t want to make him sad).
There’s a time and place for sexual come-ons.
Don’t choose immediately after the second drink in public at the bar to start rubbing my leg and creeping up my thigh in front of strangers. Don’t get wrong, I’m no prude, but save it for a bit later when we’re kinda-sorta alone.
If it’s early in and you’re on the first or second date, it’s incredibly important to have a sense of timing. You don’t want to creep him out, or worse assume you’re in it just for the sex. A guy who after the first hour of meeting him tells you he’s a bottom then starts rubbing your thigh is only looking for one thing—he might as well be on Grindr. Don’t let him assume you’re like that.
Understand his limits without judgment.
We all have different limits, which you, as a mature individual, need to accept and have compassion for. For example I know a guy who went out on a date with a guy who hated the word “queer” (I mean hated). My friend didn’t understand it, so therefore his date was wrong. He tried to convince him all the ways why it was an okay word—it was funny at first, but then it got to an awkward place. Clearly my friend lacked any kind of compassion for him, and the guy saw it. The second date did not happen.
The point here is to choose your battles by holding your tongue. It’s one thing going on a date with a guy who hates a particular word, or phrase, or band, or color or child; but it’s something completely different to take it personal for no reason. Unless they’re in a cult that is against everything you stand for, there’s always wiggle room to forget it for the sake of the date.
Keep in touch if you’re truly interested.
Don’t leave him (or yourself) hanging by a string. You might not know how he felt about it, but you do know how you feel—nothing wrong in letting him know. Make him aware of where you stand and how you feel towards him, then let him decide how he feels.
Nowadays playing hard to get isn’t the same. If you don’t ever respond, we take it as “not interested” rather than “oh he’s trying to pull me in.” Don’t play games if you’re truly interested. There’s a way of showing how you feel without making yourself too available.