Real stories about dating and relationships in New York City. Truth is more interesting than fiction.

I Just Don’t Know

I’ve had over 12 hours to think about it and I still have no idea what to think about last night’s date (OK, I was sleeping for at least 5 of those hours, but still).  I do, however, have a nickname for the guy.  That’s a no-brainer.  He’s Coach.

I can’t tell you too many details about Coach because it’s entirely possible that someone who knows him reads this blog, and his bio is pretty distinctive.  But here’s some info:

  • He was a college athlete (the type that was recruited aggressively by many schools/had a free ride) and then played his sport professionally after college – overseas.  I won’t say where or what sport, other than to say it’s a sport I LOVE and I mention how much I love this sport in my profile.
  • He now works in a field I have a lot of respect for.  A lot.
  • He’s very attractive but does not come off as cocky.
  • He has a teen-aged child who he is very close to and spoils rotten.
  • He is VERY close to his family and is a self-admitted mamas boy. He mentioned his mother more times during our than most guys would mention in several months of dating.

So, about the date.  I was charmed by him online.  He came off as sweet and unassuming, but also hot as hell (I’m not really into athletes, but am kinda tired of arty guys who won’t watch a game with me because they’re not into sports).  But then, he lost major points by not actually planning the date.  He left it completely up to me, saying “tell me when and where”.  It pissed me off.  I suggested a place and time and he agreed and I thought we were set.

And then he was late.  I got a text from him a few minutes after he was supposed to show asking where the place was again, that he’d lost the email and couldn’t remember.  I answered back with the address.  He was blocks away.  Ugh, right?  This went back and forth several times until he arrived about 20 minutes late.  By then I was in, ‘I don’t care how you are, you’re a dumbass’ mode.

But then he was charming.  Very charming.  And sweet.  And he actually argued sports with me (well, his sport).  We had a great little arguement over teams and players and stats and he took me and my opinions seriously and that was fun.  I like mixing flirting with arguing over sports (see, guys, I’m even cooler than you thought).

Only he kept bringing up his mom and his family and little things about how close they all were and how spoiled he was (he’s the only boy) and how, if he and I worked out I’d love his grandmother’s cooking and where I’d sit at the Thanksgiving table.  The sitting at the Thanksgiving table thing really was wierd.  And he asked me out for a less than an hour into the night.  Before we finished our first drinks.

Anyway, it’s nice to have someone openly express how much he likes me.  And to say, repeatedly, how much he’s looking for a relationship.   I mean, that’s what I’m looking for.  But at the same time, I’d never talk about the future like that with a guy who hadn’t already expressed deep feelings for me.  Never.  Not even jokingly.   So it kind of freaked me out when he did it.

And then, well, how much can he like me?  We just met.  Right now, he just likes the way I look (And he complimented me a couple more times than I’m comfortable with, btw.  I’m not that hot.).

Alright, I’m overthinking this.  I know I am.  Our second date is Sunday night.  I’ll learn more about him then.  For now, all I really know is that I just don’t know.


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27 to “I Just Don’t Know”


  1. SpikeTheLobster says:

    Sounds like the sort of guy who’d end up wanting you to be his second mom….

  2. PiscesInPurple says:

    The family stuff is a bit of a red flag. I’ve been burned by that, more than once. But that’s just me…

  3. recklessstudio says:

    You’re over thinking. Stop.

    This guy may actually like you and he’s being more transparent than most guys that you have dated. That doesn’t make him better or worse. It makes him different.

    And it seems like you may be interested in him for the same values that he openly mentioned and you somewhat question for mentioning quickly.

    I say hold back judgment, see him again and have a good time, which it looks like you did.

    And I like the nickname “Coach.” I have a few friends that call me that. I think it’s funny.
    I’m glad you had a good time. You’ve been due for a good date.

  4. recklessstudio says:

    Although, I should add this. I think that It’s great to have family as a priority and it should always be that way – until you have one of your own (or at least think you can start one with the one you’re with).

    Of course, barring it doesn’t get in the way of a healthy relationship.

  5. amberying says:

    Sounds like he’s moving too fast for your comfort.

  6. starangel82 says:

    I’m on the fence with this.

    Part of me says you are overthinking. You seemed to have a good time, minus his running late. You’ve been on a series of bad dates, so you may be mentally trying to sabatoge a good date because you don’t think you are due a good date. (Believe me, I’ve done that.)

    Part of me says red flag. Like I said last night, he may just be over excited because he really likes you or he may just be super close to his family. Then again, he could ask you to marry him next week. Who knows.

    I think you should hold judgement until the second date then see how you feel.

  7. jenmata says:

    This sounds so much like the approach the guy I was recently dating had. Making plans into the future, repeatedly complimenting me and saying how much he liked me. To then three weeks later, after I’m game, come with the “I don’t know how to say this, but I think we’re should be friends” speech. I tell you, I for the life of me do not get it. Not at all.

  8. Anonymous says:

    He isn’t real. He has a fantasy and because you superficially fit the part, he’s slipped you into it. I suppose it’s possible that things could “work out” if the real you and his fantasy of you aligned.

    If you have your eyes open, no reason not to see him again, but I’d ignore the future talk (change the subject!) and keep expectations very, very, very low.

  9. Roger S. Gil, M.A. says:

    Sounds promising & I agree with “recklessstudio” about the ‘overthinking’ part. It was a 1st date. While it can be a HUGE predictor of whether or not a relationship develops, it’s still WAY too early to make any judgments. Trust your instincts about his “basics”… if he past that test, things like his relationship to his family of origin, how he treats women, etc. will emerge as you date him (if you continue).

    Aside from that, my “clinical spidey-sense” was activated when you said, “he’s looking for a relationship. I mean, that’s what I’m looking for. But at the same time, I’d never talk about the future like that with a guy who hadn’t already expressed deep feelings for me. Never.”… I’m legally not allowed to “assess” those types of statements but I’ll say that these types of statements tend to be VERY revealing… not because of the actual content, but because of the underlying implications (think, “I want a future, I just don’t want to think ‘logistics’ it right now”)… tat is all. lol.

    Good luck

  10. Bob Eckstein says:

    You just described my friends…early 40′s, single, good-looking, very charming & sweet, Mom obsessed, clumsy dating skills (late, doesn’t plan, inappropriate rushing). And this is why Mr. Coach and my friends are still available–these irregulars/bargains on the dating market shelves require a bit of tolerance. My one woman friend just married my cousin who fit the bill you described. She just decided to ignore these flaws and not try to change him.

    I suggest you hint to him his dating shortcomings and play hard to get until he plans a prompt second date without “Mom.” Good luck–I actually did same with my wife who initially displayed some red flags. She got her ducks in a row and romanced me!

  11. queenieNYC says:

    I am of two minds about this.

    As someone who is very, very close to her family (my brother lives here in the city, we speak every day, and he’s one of the best friends I have), I think it’s really, REALLY annoying that people automatically get freaked out when you mention your family on a first or second date.

    I mean, I’m not going to bring up my parents’ divorce, but I might have a funny anecdote to tell involving my mother, or might mention some of the theatre stuff my brother does. I don’t do it to freak men out; I do it because my family is such an integrated part of my life that deliberately not mentioning them feels…odd.

    That said, it sounds like this guy went a bit overboard. I might tell the story of how I learned to skeet shoot on a Thanksgiving trip and surprised myself and my family by being a good shot. But I’m NOT going to talk about how great it will be when gentleman X comes along next year.

    I have noticed that, for some reason, people find it creepy/desperate (but definitely genuine) when women do this, but disingenuous/part of a campaign to get into your pants when men do it.

    I say don’t worry about it. Don’t forget about it – it might end up being part of a weird pattern – but, for now, it’s only one data point, and may only seem significant since you have so few pieces of information at the present time.

  12. snowman expert says:

    Sorry, not sure why I have a woman’s profile instead of me in my comment above; Bob Eckstein, so just posting this follow-up.

  13. recklessstudio says:

    Wow…the comments here are actually quite surprising

  14. SINgleGIRL says:

    OK, rushed through some things so I could steal some time to comment back. You guys are all great. I may not get to everyone/everything but here’s a start.
    -SpiketheLobster
    It totally didn’t occur to me that he could be looking for someone to mother him. But now that you mention that it seems plausible (based on some other things I didn’t mention in the post) and let me say I am SO not looking to be anyone’s mom. Not one bit.
    -PiscesInPurple
    This is new territory to me. I’ve HEARD of mamas boys but never actually dated one. ???
    -recklesstudio
    I absolutely am overthinking. I do that. I know. I’ve tried meditation. Not good at it, or something. And yes, I am totally going to try to go into this second date with an open mind.
    -amberying
    That’s one way to look at it. I’m used to guys moving too fast, but it’s a different kind of too fast (you know, the let’s go back to my place right now, too fast).
    -starangel82
    I have been on a series of bad dates. And that does color a girl’s judgment. Another thing to think about, but not too much because I’m already thinking too much.
    -jenmata
    Ouch. I’ve been on that ride. With rainbows and flowers and wild plans for the future. And then the cold down. Bad ride. I’d like to think that this isn’t that. Or that if it is I’d know enough to stay away from early on. Ugh.
    -Anonymous
    The cynic in me (which is a very loud voice in my head) says that what you wrote makes a lot of sense. A lot.
    -Roger Gil
    Welcome to the blog. LOL. I think most/many women are rather guarded when talking about the future with guys until they have already expressed genuine interest in us. We’ve been told so many times (so many) that talking about the future or our desire for a serious relationship might spook a guy and send him running. Heck, even saying we want to be exclusive is considered a taboo (the comments from when I first started seeing Mr. Potential and told him that I wasn’t going to be dating other people because we were sleeping together were bizarre). Anyway…

  15. derek7272 says:

    Given he added the provisio, “if he and I worked out I’d love his grandmother’s cooking …” I don’t really think it’s that weird or clingy or that you should read too much into it.

    Obv., I wasn’t there, but maybe it was even a throwaway line? Like he’s just telling you what’s important to him and what he brings to the table — not that he envisions introducing you to grandma anytime soon. Well, maybe.

  16. onedatewonder says:

    I will be honest and tell you up front, this comment is brought to you by 5 years (one and a half of them married) with a mama’s boy.

    Watch out for that nonsense. There’s loving your family, and LOVING your family. The latter is creepy and wrong. If mama ends up knowing everything about his relationships, then nothing good can come of such nonsense.

    Also, I don’t care what anyone says, the words “If we work out…” uttered on a first date equal some kind of weird clingy nonsense ahead. It’s easy to be romanced by someone who wants a relationship. But there is a very fine line between wanting a relationship and wanting a relationship WITH YOU. Unfortunately bold statements like that point to the former rather than the latter. That is also something to watch.

    All in all, I say proceed with caution. Dude needs to tone it down a little. And you need to make sure it’s you he wants and not just a desire to be all coupled up.

  17. cjw666 says:

    Well, you other guys are all obviously right – for you (each of you personally). For SINgleGIRL: I thought that was the point of dating – you don’t know till you get to know, over time … so you date. To start with at least. Then, later on, you date ‘cos you want to go on … or not! If you’ve found another that you think is worth finding out about, that’s a plus, surely.

  18. derek7272 says:

    I’m sure I’ve said that phrase before – “if we work out,” you’ll get X, Y or Z. “If we work out, I’ll take you on a lot of my business trips to Paris!” I think it’s more about trying to paint of picture of what life with me would be like, and suggest what I would bring to the table.

    But admittedly, I’ve been all about giving these Internet guys the benefit of the doubt, and so far I’ve been mostly proven wrong. So we’ll see!

  19. Shannia says:

    you’re overthinking this, if you had a good time, enjoy. Hopefully the 2nd date will be better. Hemight just be a clumsy dater … and a mama’s boy.

  20. SINgleGIRL says:

    -Bob Eckstein/snowman expert
    I hadn’t at all thought of the coach in that context. I’m always willing to give a bad dater a little extra room/another chance or two. I’d rather be with a genuinely decent guy that sucks at dating than a jerk that’s great at dating. It’s the mom-obsessed thing that I don’t know about. Mom-obsessed? That’s considered just irregular, not outright weird?
    -queenieNYC
    I’m completely cool with a guy who’s close to his family (in fact, I consider that kind of attractive). It was the mammas boy part of it that I found unattractive and the fact that his mom seemed to still have a huge influence in his life (more than I would be comfortable with). But I’m willing to wait to see if I misinterpreted that. i could be completely off base. It happens.
    -derek7272
    It surprises me to hear that anyone would say something like, “if we work out we’ll travel to Paris together” on a first date. I guess that just seems very, I don’t know, the kind of thing that would be a red flag for me. It’s your norm and clearly hasn’t freaked out your past girlfriends, but I’m of the mind that I really want to keep things in the present tense until there is an actual relationship. As a rule of thumb, I don’t want to hear about something we might do together in the future until we’ve had sex and I’ve decided a guy’s a keeper. And even then, it might be too soon.
    -onedatewonder
    Yep. And yep. You are speaking to my fears – dead on. And thank you for getting it. And I’m sorry re your ex. That kinda sounds horrible.
    -cjw666
    Thanks sweetie. It is a plus that he’s worth a second date. It’s been a little while since one of those. And so we’ll see. *Fingers crossed*
    -Shannia
    LOL. It’s either one fo the other. Hopefully I’ll find out on Sunday (our second date is Sunday night).

  21. KrisN says:

    Hey, thanks for the post… This seems to be a common problem for me in dating, particularly lately. I find that the men I date fall into two categories. 1. They come on too strong too fast (example: You smell so good- it is permanantly engrained in my mind forever) or 2. They are totally unavailable (whether either of us realize it at the time). I find myself much more attracted to the latter and lately I have been trying to figure out why.

    As women, we have been brought up with the ideal fantasy of what a relationship is. and could be. I can only speak for myself but I have imagined a guy telling me I smell amazing, or that he sees me as part as of his family or that he wants to be in a committed relationship with me a thousand times. There is a BIG difference between my fantasy and my reality… which might I add is exactly why they call it a fantasy. I have my theories on why guys that come on too strong freak me out… but I would certainly love your take.

    And about the mothering and the mama’s boy thing…. if you think he’s bad. Just wait until you meet her! Its 10 times worst. I dated a guy for 4 years who, if his mom could would still have all of her kids living under her roof (and the oldest is 40 and married). Good Luck!

  22. Tokyo Cowgirl says:

    Initially I was going to leave an excited comment with a whole bunch of exclamation points about how fan-freaking-tastic it is that you seem to have found a winner, or at least someone I’m enthusiastic for you to proceed to Date Number Two with.

    Then I skimmed through some of those “OH MY GOD STOP EVERYTHING RIGHT NOW” comments from the Chicken Littles out there, most of whom (not so coincidentally, I fear) happened to be women, and now I sort of feel like I need to get on top of my soap box for a wee second and lecture.

    If I had listened to all of the people in my life who told me that every little warning sign was legitimate and I should never settle for anything other than perfection, do you know where I would be right now?

    Single. Like them.

    Not that there is anything wrong with that, of course, but I’m a lot happier these days than I was during those days.

    I’m really freaking picky about the kind of people I date long term, so picky in fact that I will usually go months at a time without ever going out on a date. So, knowing that, when I find someone that meets those qualifications I tend to let little things pass. Sure, the obvious red flags (abusive tendencies, alcoholism, sexual indiscretions) are immediate road blocks, but the whole mama’s boy thing? Forgivable.

    As for complimenting you too much?

    Would you prefer the alternative?

    I think not :-)

  23. derek7272 says:

    For all I know it did freak my date out and was a red flag for her … things did not, in the end, work out. But ultimately I think while I have my share of flaws, being clingy is not among them … I’m probably more aloof. I guess it’s hard to draw conclusions about someone based on one remark..

  24. onedatewonder says:

    Tokyo Cowgirl, you think it’s forgivable now. And you probably will continue to do so. Right up until you have a fight with your husband and end up on the phone with your mother in law (who called you) yelling at you for wronging her darling son. Then you will understand why people have a problem with it. Or maybe you won’t and you’ll let her yell. But personally, I hung up on the woman.

  25. Veka says:

    I have to agree with Tokyo Cowgirl. I couldn’t have said it better myself. He sounds like a decent guy, and IMO it’s too early to write him off. My mom has this phrase she always tells me: Expectations are 85% of the outcome. I’m not going to tell you to have a positive attitude about the 2nd date, but don’t have a negative one either! So, enjoy your 2nd date & let us know how it goes! :)

  26. SINgleGIRL says:

    -KrisN
    I know exactly why I get freaked out by guys who come on very strong. Because I’ve fallen for it in the past. Hard. Really, really hard. Not the cheesy ‘you smell good’ lines but the whole package of attentiveness from day one and constant, seemingly sincere compliments and the plans for the future before they’re really appropriate. And each and every time the rug got pulled out from under me. I’m not going to say it was always fake, or an act. But that maybe men have come on too strong because they wanted to WIN me over and once they won me they put the A game away and well. Please refer to my post on boys and men. From The Frisky post “A boy wants what he wants until he gets it, and then he doesn’t want it anymore.
    -Tokyo Cowgirl
    I’m really happy you’re happy in you’re relationship. I’d like to find a relationship that I can be happy in. But barring that, I’d rather be single. Period. As you know, a blog amplifies passing thoughts. I am concerned, MILDLY, that Coach is a mama’s boy and what that might actually mean in practice. Because I really don’t know. I haven’t spent more than 30 minutes thinking about it since our date, and that includes the time I’ve used to write the post and respond to the comments. It’s just a thought I have in relationship to him. If it turns out that he can’t make decisions without consulting his mother, then we won’t be dating long. Whatever. It was just one date.
    -derek7272
    Who said you were clingy? I said red flags. Big red flags. To me. Everyone has different red flags. Everyone is looking for something different in relationships and partners. Viva la difference.
    -onedatewonder
    I wouldn’t have made it to the end of the call before hanging up. But then, I have a really low tolerance for that type of thing.
    -Veka
    Well, I’m glad you think he sounds like a decent guy. t think he probably he is, which is why I accepted a second date with him (otherwise?). But I don’t believe that expectations predict outcome. Nor do I believe in The Secret or the Laws of Attraction. I don’t belittle people who do, just wish to be left to believe in my good old fashioned world of chaos and sorrow. I am going into tomorrow’s date hoping to get to know him better. Nothing more. That’s neither positive or negative in my book.

  27. angelbaby2 says:

    you are way too picky. just go on the date and have fun.