Advice

Get online dating tips, tricks, and ideas. Learn how to improve your profile, live a healthy dating life, and get a date in Boston.

Charity's First OkCupid Date: She Gives Us The Juice!

The last time we talked to Charity she was getting ready to go on a date with a guy she'd nicknamed Vanilla.

Charity's gone on the date, and now explains how to dress, how physical to get, and how to handle the bill.

What was he wearing? Did you like it?

Vanilla was wearing khakis, and an argyle sweater with a nice shirt underneath. Business casual. I made a joke about wearing argyle to a dive bar, but he looked very nice and was much better looking IRL than in his OkCupid photos.

Did he seem nervous?

He seemed somewhat nervous at first, but I’m a decent conversationalist and we had a lot in common, plus a bit of liquid courage, and nerves were out the window.

How did you feel about the level of physical contact?

He nailed it. We greeted with a hug and he kept his arm on the back of my barstool, but left it at that. Prude? Maybe. I wasn’t trying to take him home. To be fair, he was a very nice looking guy, but I wasn’t overwhelmingly attracted to him so I was satisfied with that level of physical contact.

Were you ever uncomfortable on the date?

I really didn’t feel uncomfortable at all. We chose a good place for a first date because we had a drink, chatted for a while, shared a plate of nachos, then the live music band showed up so we watched them perform. Activities are good. Distractions and people watching are too. It was an ideal first date venue.

Did you offer to pay? How did you discuss the bill?

He took care of the bill. I offered to pay, but he said no in one hand motion with a quick “don’t worry about it.” I was partly expecting him to because it was our first date and he seemed like he would. Additionally, he lives at home. I don’t love it when that’s the case, but it doesn’t bother me either. However, I like the guy to foot the bill since he has fewer expenses than me.

What would be the best thing for the guy to do next? (Should he text you?)

I prefer to be more of the initiator in these situations. I’m not sure if I’m alone on this one, but when a guy initiates TOO much, I start to feel smothered and stop texting back. So Vanilla kept it real, we chatted for a few days and despite the great date, it fizzled out.

On to the next one!