Serious Questions

My schedule for the two-week period ending this coming Saturday includes the following highlights:

Wednesday, 9/24 – Date planned. (Date cancelled – may become a story later depending on followup)
Friday, 9/26 – 3rd date with A (a non-bad-date story in the making)
Sunday, 9/28 – Speed dating event!
Wednesday, 10/1 – Reschedule from 9/24 – blind date
Friday, 10/3 – 2nd date dinner planned with B (a non-bad-date story in the making)
Saturday, 10/4 – 4th Date planned with A

That’s over an 11-day span, and represents 6 different evening commitments, with 5 actual evenings spent doing date-related things. Mind you, I structured this to be a busy weekend deliberately, since it’s my ex’s weekend with the kids (the following weekend, my date availability will be Zero), but it is still a bit exhausting!

There are a lot of other things I want to try, but my life is feeling very crowded!

So many dates!

So many dates!

Part of this, of course, is that I am actually moving on to second dates with some people, which is… phenomenal. Really.

There are questions I did not consider before coming into this.

What happens if things become serious? How do I define serious? How many guys am I comfortable casually dating at a time? How do I define the dating time window? If I have a blind date scheduled for three weeks from Wednesday, does he count against my total? How often should I be seeing someone I’m casually dating? How do I walk away? How do I decide to walk away?

I think at least some of these need at least working answers now, so here goes:

How do I define serious?


I don’t necessarily think serious and exclusive have to be the same thing. I think I can be serious about a guy — serious enough that I’m not comfortable being serious with anyone else — and still date casually. Serious means that at the end of a date, I don’t feel like I have to ask, “Do you want to get together again?” Serious means that if I want to stop, I feel it’s necessary to break up, not simply to say, “Thanks, but I don’t think this is going anywhere, so we should just stop now.”

I think significant physical intimacy, for me, is sufficient but not necessary to make something serious.

Does serious have a time component? Well, I think if I’m at date three or four and not feeling like we’re getting serious, it’s probably time to hop off that bus. Obviously, I can stop earlier if it’s really clear it’s not happening.

In light of new and recent evidence (OMG I like touchy kissy stuff! Who knew??) I’ll add that if by date three or four I’m not starting to at least seriously think about touchy kissy stuff, that ship is veering into iceberg territory. Probably not worth continuing.

Serious means: he knows at least the major parts of my “dating baggage”. Three kids, regular churchgoer, still living with my parents. He is at least okay with these, and doesn’t make snarky comments about any of them. Again: date four deadline. If we haven’t gotten to these conversations yet, then I don’t really trust him enough to open up, and we’re not going anywhere.

What are my casual dating rules?

If I’m serious-but-not-exclusive with someone, I can still date. I can go on my stupid paid-way-too-much-for-these blind dates. I can speed date. I can go to classes or parties or events and try to meet fun people. I can go out with these guys for drinks or dinner or dancing or whatever.

Within certain reasonable limits.

I think maybe three is about my limit. It’s not even a moral or ethical issue. It’s logistics. Honestly, I am drowning a bit this week! So much going on, so many things to keep straight… and my life is not empty other than this dating experiment, either. Every Sunday, I’m at church in the morning. Monday nights, I attend a Bible study group. I’m in the process of selling a house, which (let me tell you) is TIME CONSUMING. I have doctor’s appointments, dentist appointments, car issues…

Also, you know, three kids. Who lay claim to a big part of my time.

Three guys means that my 3 kid-free weekend days in every three-week period can be spread out a bit. I have time for afternoon dates (an extra 3 per 3 weeks) and the occasional weeknight (with childcare support).

I will start guys on my counter at the beginning of the week I’m scheduled to date them. So tonight’s blind date counted yesterday, but not last Thursday. However, if someone else had come into the picture last Thursday, I’d have been obligated to cancel today’s date.

Online chatting does not count until and unless there’s a hard date nailed down for meeting in person.

How do I walk away?

With kindness, and with clear communication. “I’ve enjoyed our dates, but I don’t think this has long-term potential. I wish you the best of luck in everything, but I’m not going to be going out with you again.” OR: “I’m really just not feeling this. You’re a good guy, but we’re just not clicking in the way that I need. Best of luck.”

I’m not sure how/when/where to do this, though. Breaking up in person has always seemed the nicest and fairest way to do things to me, until I started thinking logistics. If I’m seeing a person every week or two, and it involves days of planning and an hour’s drive to make things happen, is it really kindest to get expectations up of a good evening, then yank those hopes away? Or worse, have the date and then break up at the end, with the intention in mind all along? Or would it be better to tell him over the phone when we reach the planning stage? How do you make a date-to-break-up?

I really don’t know about this one. Thoughts?


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