Love Letters: What About A Second Date?

Monday | September 22, 2014

Love Letters Relationships

Love Letters: What About A Second Date?

Hi Meredith,

I’m in my early 20s and completely inexperienced when it comes to dating. I was never into the hookup culture at my college, and after feeling displaced after graduation, I decided to try an online dating site many people I know have had success with.

I’m very picky but was eventually matched with a guy I actually enjoyed talking to, and we decided to meet up. The night was a lot of fun — I’ve never genuinely laughed so much — and ended on a very good note. He texted me the next day and a couple days later to ask how my weekend was.

Since he has always initiated the conversations, I decided to text him and we chatted for a while, but never did the subject of meeting again come up. I’m afraid I was playing it cool for too long, not wanting to seem super clingy or forward, and he thinks I’m disinterested. Or maybe he isn’t interested anymore, in which case, why would he bother talking to me?

I don’t understand the male brain, nor do I really understand my own. I’d really like to see him again, but I don’t want to scare him away. Help!

– Worrywart, Boston

Ask him if he wants to hang out again. Just say, “Hey, do you want to have dinner this weekend?” You have nothing to lose, and you can’t keep texting and guessing about his intentions.

You asked why he’d bother talking to you if he’s not interested. The answer is: boredom. Texting is such an instant source of attention that for some people it doesn’t matter who’s on the other end of the line. In the future, if you have a good first date, keep the texting to a minimum and focus more on planning a second outing. It’s not clingy to want to see someone you like. There’s no need to play it cool.

Be clear about what you want from this guy and keep browsing that site. There might be a match who’s more interested in getting to the second date.

Readers? Did she play it too cool or is this guy just not interested enough for a second date? Should she ask him out or just let this go?

– Meredith

Relationships