When / How Often to Contact a New Date?

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I am fairly new to dating after a divorce (yes, I’ve waited plenty of time to sort things out with my ex and adjusting to life as a single dad, etc.). I am generally a confident man. I have had a fair amount of success in my career, have always maintained good social skills, and have enjoyed fostering great relationships of many kinds throughout my life (romantic, family, friendships, business, etc.).

It has been over 10 years since I have been dating, and that was in college so I know things are much different now. I have been out with several different women (mostly met through an online dating site) with varied results. All have been enjoyable – one resulted in a short fun relationship of friendly email banter during the work day, and several fun dates … but kind of fizzled eventually for no particular reason other than the chemistry just wasn’t there. In other words, I’m new to dating for sure, but I have a little and not a total neophyte. Here’s my situation/question(s)…

Recently I ran into an acquaintance (actually my daughter’s former teacher) who was aware of my divorce, and asked if I was still single (with a somewhat mischievous look …so I knew where this was going). Well,


long story made short – she had friend in the area whose husband had passed away about a year ago (this is important in that it is a different dynamic than dating another divorcee) and she was about my age, and a single mom. She was actually very close friends with the parents of one of the boys in my daughter’s class who is very good friends with my daughter. I know the parents, not well, but well enough to trust their judgment along with the teachers, so I was willing to accept the “setup”. Anyway, I gave the teacher my number and email and she was going to arrange an outing with the six of us (her and her husband, the other parents, the friend and me). That evening I had a call from the friend … she introduced herself and just said, “look we’re both adults, why go through all this arranging and setting up and I just thought we could talk and see where it goes.” (Not exact words, of course but you get the point, which is that she was very outgoing, and I really liked that). Anyhow, we chatted for a good 20 minutes or so. I happened to be out with some friends that night so I had to let her go, otherwise I suspect we would have talked longer. We arranged to meet the next night at a local winery … the date was fabulous, we had a few, but not too many drinks and the conversation was great … not one single awkward moment of silence, and it was very relaxed and comfortable … we even shared our meal (not in a “would you like to try mine” sort of way, but just naturally placed the plates between us and ate of each other’s plates as though it was something we always did). We joked and teased a lot and we both laughed quite a bit and there was even some moderate flirting. I did find her quite attractive and I believe she did me as well. She knew a lot more about me than I did her as apparently her friends (the other parents) knew me much better than I thought they did and apparently had quite a few nice things to say about me (which was very flattering).

During the evening we made plans to get together the following week at a local bar, with bocce ball courts for a good competition since we both have competitive spirits. This, of course, was complete with lots of smack-talking about how we were going to kick each other’s butts, etc. She was going out of town for the weekend with her kids and said she would call me the following Tuesday so we could nail down our plans. The night ended with a nice kiss (which she initiated … not because I didn’t want to, but just because I don’t kiss on a first date … that’s fine when you’re 20 or so, in my mid-thirties, it just seems very unnecessary … there’ll be plenty of time for that sort of thing later, right?). I did follow up with a text message the next day, just letting her know how much I enjoyed the evening and that I was looking forward to getting together again next week. (I made slight joke apologizing for the text and juvenile it is.) She replied immediately that she thought my text was very sweet and she felt the same way and that is ok to text anytime.

So … now the weekend has gone by and I have thought about her several times. In fact, I had another date Friday night that had been previously scheduled and that poor girl didn’t stand a chance because I was a little smitten with my date the previous night. I thought several times over the weekend of sending a cute or witty text just to say HI and let her know I was thinking about her and even thought of calling tonight, but everything I read tends to indicate that that shows signs of over-eagerness, and given that we already have a plan (she said she’ll call me Tuesday … let’s leave well enough alone, right?), but I am not much for games, yet alone rules and if I feel like calling, I should right? She’s gone through a rough time over the last year (well we both have) and I get the sense that she’s been out with a few “winners” lately and she is just looking for a good time at this point … as am I. Anyhow, I never called or texted her … but I kind of feel like I should have. I don’t want her to think I’m playing the “wait three days to call” game or anything like that, because my instinct is that she’s not into that kind of thing. She is smart and confident and doesn’t have time for games … nor do I for that matter, yet I can’t help but remain perplexed over what the right move is/was here. Am I making this complicated or is that just how it is? The reality is I sincerely can’t wait to hear from her and I am very excited for our next date, which is something I have not really experienced in long time. At the same time, I am so concerned with making a mistake that I did not act at all, which is very much against my nature. The weekend has lapsed now and there is no way I can call her tomorrow as I have too much going on work-wise, thus I am definitely waiting until Tuesday at this point when she is supposed to call – did I make a good choice here?

Beyond that, let’s assume that we have our second date (which I believe is a safe assumption) now after that, what is the protocol? At what point should things evolve into more casual and regular contact beyond just connecting to plan the next date? All the advice seems to lean toward, let it happen naturally, yet also toward don’t be over-anxious to make the next contact … what if the natural instinct is to make a “just to say hello” phone call or text? These two prevailing pieces of advice seem to conflict with each other here.

Well … sorry to be so long-winded here. I do tend to over-analyze things like this and I am really not that worried about this particular situation … I think we hit it off well enough that things will move along just fine and if not, oh well. I am very perplexed though about the whole making contact issue in dating at this age. I am normally a very skilled communicator and it comes natural to me … I never have to think twice about when to call or not call someone … if there’s something that needs to be discussed or something I want to discuss, I do it and almost always the other party is glad I did, but for some reason, this whole dating thing has got me a little off balance so I am very interested in your reply.

MIDLIFE BACHELOR ANSWER: Thanks for writing in. This is an excellent and common question/situation for any new midlife bachelor to go through, and so I think the answers can benefit many. First of all – there was a much simpler but similar question that came in a while back – so you might consider checking it out, and read through the references within this site that are quoted:

How Soon to Call After the First Date?

Now to address your specific situation, my core advice is to simply relax and pace yourself with respect to pursuing this hot new woman. The last thing you want to do is to scare her off by being too aggressive with respect to calling her. You sound like a high-level guy with an important career – and I know how that can be taxing of one’s time … which means that it is not like you have all the time in the world to sit around and think about calling her. You’ve probably got a thousand things going on, and you are used to paying the most attention to maybe the top five … and somehow this new woman has crept into your top five action items. Even though it may be counter-intuitive for you, I’d say your best bet for this particular woman is at first to not contact her more than once every three or four days … again, just so you don’t appear over-eager, and so that you do not scare her off.

You sound a lot like me, and so I have a few more itemized thoughts for you to consider:

1) With respect to dating, in general, or this woman, in particular, try not to overthink or over-analyze – instead just keep things simple. You sound like a classic “Type A” personality (same as me), and we must fight not to obsess over details when it really is the “big picture” that matters most.

2) At the front-end of any new relationship, I suggest not overly contacting the new woman … as it could scare her off. I would probably have told her something like, “So you’ll call me on Tuesday … but if you feel like talking over the weekend, then I’ll be around” and left it at that. I don’t consider this a “game” … it is really just common courtesy. In my own past, any time a woman has called me too quickly or two repeatedly too soon … she has turned out to be a psychopath. (See Types of Women – Psycho and What Makes a Woman Turn Psycho?).

3) Take each date one date at a time … never assume anything about the nature of your relationship with her … just relax, and enjoy yourself. Oh – and don’t over-plan your dates! I used to do that (because I’m “Type A”), and it prevented me from relaxing much of the time.

4) See how your next date goes. For me – after a few dates, things wind up being fairly obvious where it is all leading.

Now one thing that you mentioned did seem a bit out of place. You said that you don’t kiss on a first date. I advise you to revisit that particular rule of yours (unless she has bad breath or jacked up teeth). I think at least a good night kiss (initiated by you) is an excellent barometer of how hot the relationship might turn out. Besides, as midlife bachelors – our golden rule here is ALWAYS GO FOR IT … which means if there is any doubt about what you should do in any given situation, then refer to that golden rule.   ha ha   Anyway, you might consider reading the section called Saying Goodnight or Goodbye on the First Date or Two in the Develop a Strategy for Midlife Bachelor Success section under Midlife Dating Advice.

Good luck – let us know how things work out. And I see that you already joined our Midlife Forum – so I look forward to hearing some good comments and perspective from you!

Avatar of Greg Smith
About the Author

Midlife Bachelor chronicles lifestyle, dating, and relationship experiences and advice to avoid a midlife crisis. Readers like you are often beyond young adulthood in their 30’s, 40’s, and 50’s that want to understand how dating, sex, relationships, and love fit in with our lifestyles.