Skip to content
Author
PUBLISHED: | UPDATED:

Welcome to “Threesome.” Each week, we’ll take a look at a relationship question from the public and have three panelists give their insights. Have a question to ask? Shoot it over to us on Twitter at @redeyechicago or on our Facebook page. If it’s a little more private, feel free to email it to redeye@redeyechicago.com with the word “Threesome” in the subject line.

QUESTION:

I’m new to dating, have spent a lot of time working on myself, and now I am trying out OKCupid.

Question is, how much do you generally text before a first date? I have a date on Sunday (my first one ever), and I basically have spent a ton of time over the last few days texting this girl even though we haven’t met yet. Is this normal? I don’t want to come across as too needy or clingy or something, and I really hope I haven’t screwed things up.

— Question from a 25-year-old man via Reddit

THREE ANSWERS:

Fred

Host of “Fred and Angi in the Morning” on 103.5 KISS-FM | Single, 34

Aside from the ability to conduct a full Google-stalk—wait, that sounds aggressive—”web perusal” of your date-to-be, one massive advantage of online dating is the inherent communication you have before actually meeting. By default, you’re almost forced to ask many background questions about your match, either because you want to keep the interaction going or because the more information you obtain, the more confident you feel that you’re chatting with a real person and might not wind up on an episode of “Catfish” (while there are no guarantees).

When I think of the last few set-up dates I have been on in comparison with dates initiated through a site or an app (yeah, I’m on Tinder), the difference in the depth of communication is vast—I know far more about the women I have met online before physically meeting them. So don’t shy away from pre-date texting. It’s likely it will make for a more comfortable first date. But maybe mention the stuffed animal with which you sleep a little further down the road…

—Fred | @fredonair

EXTRA: Advice on surviving everything post-college, from that crappy first job to singledom

Keri Wiginton

Photo editor and part-time advice giver at the Chicago Tribune | Married, 33

If she is still responding, then it’s fine. Back in the old days, most people would have multiple phone conversations before going on a date. The invention of texting and its pervasive use in society have made many an introvert’s life better. I hate the phone. Actually, “hate” is putting it lightly. Abhor, loathe or despise is more accurate. But I digress.

I would think contact before the date would show your interest, but definitely don’t overdo it with messages every five minutes. Leave a little intrigue. To get some additional opinions, I farmed this question out to a few female colleagues:

“Here’s the problem though, if they’ve already been texting nonstop and he stops texting her, it will be awkward. It’s also pretty unromantic. He should just be like, ‘Excited to see you,’ make sure plans are set, and leave it at that. —25, single

“I agree that it’s fine if she’s still responding, but if he notices she’s taking a weirdly long time to write back, maybe he can slow it down.” —27, married

“If he’s not getting signals or clues that he should cool it on the texting, it’s fine. Don’t overthink it, dude.” —30, married

—Keri | @keriphoto

Michelle Lopez

Designer, web editor for The Mash | Married, 31

Props to you! Being new to anything can be intimidating and scary, but dating? It can get wild out there. It sounds like you are definitely on the right track, though—working on yourself is the best possible prep for this journey you’re about to begin.

It’s been a while since I had a first date, but I fully understand your concern. You’re worried about being perceived as—what’s the word the kids say? “Thirsty.”

Don’t fret about this textual relationship. It’s not necessarily a bad thing. This is your chance to showcase your dazzling personality and tease your charm and wit before the date.

What matters most is that you feel confident and comfortable in what you’ve been texting. Are you blowing up her phone with flirty conversation? Or are you texting her every two hours with “Sup?” More importantly, is she texting you back and engaging with you? The key here is maintaining a delicate balance of expressing interest and excitement for the date, and at the same time preserving some semblance of mystery that she can look forward to on Sunday.

I think you’re being too hard on yourself. If you keep second-guessing everything you do, dating is not going to be a fun ride. She probably would have canceled the date by now if she really felt that you were needy or clingy, right?

If this is truly your texting style and she wasn’t receptive to it, then she wasn’t going to be a good match for you anyway. On to the next one—keep calm and OKCupid on.

—Michelle | @michelleglopez